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CAS 73-24-5

6-Aminopurine9H-purin-6-amine

Codes: Tenofovir disoproxil phosphate-008, TENO-001, ADEF-003, (III)70439-1-a, (I)70439-5-a

Application context (from source-drug indications)

HIV infectionLamivudine/Tenofovir Disoproxil FumarateChronic hepatitis BLamivudine/Tenofovir Disoproxil FumarateHIV infectionEfavirenz/Lamivudine/Tenofovir Disoproxil FumarateHepatitis BTenofovir Alafenamide FumarateChronic hepatitis BTenofovir Alafenamide FumarateRelapsing-remitting multiple sclerosisTenofovir Alafenamide FumarateFatigueTenofovir Alafenamide FumarateHIV infectionTenofovir Alafenamide FumarateChronic hepatitis CTenofovir Alafenamide FumarateHIV infectionEmtricitabine/Rilpivirine Hydrochloride/Tenofovir Disoproxil FumarateHepatitis BTenofovir disoproxil phosphateHepatitis BAdefovir DipivoxilChronic hepatitis BAdefovir DipivoxilHIV infectionAdefovir DipivoxilLiver transplant rejectionAdefovir DipivoxilHepatitisAdefovir Dipivoxil巨细胞病毒感染Adefovir Dipivoxil巨细胞病毒感染Vidarabine MonophosphateHerpesvirus infectionVidarabine Monophosphate

Source drugs (routes using this intermediate)

DrugTierExpiry
Lamivudine/Tenofovir Disoproxil FumarateTier C — Watch / trade-
Efavirenz/Lamivudine/Tenofovir Disoproxil FumarateTier C — Watch / trade-
Tenofovir Alafenamide FumarateTier B — Position early-
Emtricitabine/Rilpivirine Hydrochloride/Tenofovir Disoproxil FumarateTier B — Position early-
Tenofovir disoproxil phosphateTier C — Watch / trade-
Adefovir DipivoxilTier C — Watch / trade-
Vidarabine MonophosphateTier C — Watch / trade-

Position in synthesis routes (up/downstream chain)

Ordered by route registration; left → right is the synthesis direction. The highlighted node is the current CAS; others link to their own profiles.

Lamivudine/Tenofovir Disoproxil FumarateOptimised routesteps: 11total yield: 23.3g(Tenofovir disoproxil phosphate (API))
Chloroacetyl chloride→1-Chloro-2(R)-propanol→Diethyl (tosyloxy)methylphosphonate→Diethyl (chloromethyl)phosphonate→Diethyl phosphonate→Diethyl phosphonomethanol→Diethyl (2-chloro-1(R)-methylethoxy)methylphosphonate→6-Aminopurine→(R)-9-[2-(Diethylphosphonomethoxy)propyl] adenine→(R)-9-(2-Phosphonomethoxypropyl)adenine→Chloromethyl isopropyl carbonate→Bis[[(isopropoxycarbonyl)oxy]methyl] ([[(2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy]methyl)phosphonate→2(R)-Methyloxirane→(R)-(+)-9-(2-Hydroxypropyl)adenine→(R)-Propylene carbonate→(S)-Glycidol→(R)-1,2-Propanediol
Lamivudine/Tenofovir Disoproxil FumarateOptimised routesteps: 4total yield: /
Propane-1,2(R)-diol→(4R)-4-Methyl-1,3-dioxolane→N,N,N',N'-Tetraethylphosphorodiamidous chloride→P-([[(2R)-1-Chloropropan-2-yl]oxy]methyl)-N,N,N',N'-tetraethylphosphonic diamide→6-Aminopurine→P-([[(2R)-1-(6-Amino-9H-purin-9-yl)propan-2-yl]oxy]methyl)-N,N,N',N'-tetraethylphosphonic diamide
Efavirenz/Lamivudine/Tenofovir Disoproxil FumarateOptimised routesteps: 11total yield: 23.3g(Tenofovir disoproxil phosphate (API))
Chloroacetyl chloride→1-Chloro-2(R)-propanol→Diethyl (tosyloxy)methylphosphonate→Diethyl (chloromethyl)phosphonate→Diethyl phosphonate→Diethyl phosphonomethanol→Diethyl (2-chloro-1(R)-methylethoxy)methylphosphonate→6-Aminopurine→(R)-9-[2-(Diethylphosphonomethoxy)propyl] adenine→(R)-9-(2-Phosphonomethoxypropyl)adenine→Chloromethyl isopropyl carbonate→Bis[[(isopropoxycarbonyl)oxy]methyl] ([[(2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy]methyl)phosphonate→2(R)-Methyloxirane→(R)-(+)-9-(2-Hydroxypropyl)adenine→(R)-Propylene carbonate→(S)-Glycidol→(R)-1,2-Propanediol
Efavirenz/Lamivudine/Tenofovir Disoproxil FumarateOptimised routesteps: 4total yield: /
Propane-1,2(R)-diol→(4R)-4-Methyl-1,3-dioxolane→N,N,N',N'-Tetraethylphosphorodiamidous chloride→P-([[(2R)-1-Chloropropan-2-yl]oxy]methyl)-N,N,N',N'-tetraethylphosphonic diamide→6-Aminopurine→P-([[(2R)-1-(6-Amino-9H-purin-9-yl)propan-2-yl]oxy]methyl)-N,N,N',N'-tetraethylphosphonic diamide
Tenofovir Alafenamide FumarateOriginator routesteps: 6total yield: 1.329 kg
9H-purin-6-amine→(R)-4-methyl-1,3-dioxolan-2-one→(R)-1-(6-amino-9H-purin-9-yl)propan-2-ol→(diethoxyphosphoryl)methyl 4-methylbenzenesulfonate→(R)-(((1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)phosphonic acid→phenyl hydrogen ((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)phosphonate→isopropyl L-alaninate→isopropyl (((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)(phenoxy)phosphoryl)-L-alaninate
Emtricitabine/Rilpivirine Hydrochloride/Tenofovir Disoproxil FumarateOptimised routesteps: 11total yield: 23.3g(Tenofovir disoproxil phosphate (API))
Chloroacetyl chloride→1-Chloro-2(R)-propanol→Diethyl (tosyloxy)methylphosphonate→Diethyl (chloromethyl)phosphonate→Diethyl phosphonate→Diethyl phosphonomethanol→Diethyl (2-chloro-1(R)-methylethoxy)methylphosphonate→6-Aminopurine→(R)-9-[2-(Diethylphosphonomethoxy)propyl] adenine→(R)-9-(2-Phosphonomethoxypropyl)adenine→Chloromethyl isopropyl carbonate→Bis[[(isopropoxycarbonyl)oxy]methyl] ([[(2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy]methyl)phosphonate→2(R)-Methyloxirane→(R)-(+)-9-(2-Hydroxypropyl)adenine→(R)-Propylene carbonate→(S)-Glycidol→(R)-1,2-Propanediol
Emtricitabine/Rilpivirine Hydrochloride/Tenofovir Disoproxil FumarateOptimised routesteps: 4total yield: /
Propane-1,2(R)-diol→(4R)-4-Methyl-1,3-dioxolane→N,N,N',N'-Tetraethylphosphorodiamidous chloride→P-([[(2R)-1-Chloropropan-2-yl]oxy]methyl)-N,N,N',N'-tetraethylphosphonic diamide→6-Aminopurine→P-([[(2R)-1-(6-Amino-9H-purin-9-yl)propan-2-yl]oxy]methyl)-N,N,N',N'-tetraethylphosphonic diamide
Tenofovir disoproxil phosphateOptimised routesteps: 11total yield: 23.3g(Tenofovir disoproxil phosphate (API))
Chloroacetyl chloride→1-Chloro-2(R)-propanol→Diethyl (tosyloxy)methylphosphonate→Diethyl (chloromethyl)phosphonate→Diethyl phosphonate→Diethyl phosphonomethanol→Diethyl (2-chloro-1(R)-methylethoxy)methylphosphonate→6-Aminopurine→(R)-9-[2-(Diethylphosphonomethoxy)propyl] adenine→(R)-9-(2-Phosphonomethoxypropyl)adenine→Chloromethyl isopropyl carbonate→Bis[[(isopropoxycarbonyl)oxy]methyl] ([[(2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy]methyl)phosphonate→2(R)-Methyloxirane→(R)-(+)-9-(2-Hydroxypropyl)adenine→(R)-Propylene carbonate→(S)-Glycidol→(R)-1,2-Propanediol
Tenofovir disoproxil phosphateOptimised routesteps: 4total yield: /
Propane-1,2(R)-diol→(4R)-4-Methyl-1,3-dioxolane→N,N,N',N'-Tetraethylphosphorodiamidous chloride→P-([[(2R)-1-Chloropropan-2-yl]oxy]methyl)-N,N,N',N'-tetraethylphosphonic diamide→6-Aminopurine→P-([[(2R)-1-(6-Amino-9H-purin-9-yl)propan-2-yl]oxy]methyl)-N,N,N',N'-tetraethylphosphonic diamide
Adefovir DipivoxilOptimised routesteps: 4total yield: /
((2-(6-amino-9H-purin-9-yl)ethoxy)methyl)phosphonic acid→chloromethyl pivalate→9H-purin-6-amine→1,3-dioxolan-2-one→2-(6-amino-9H-purin-9-yl)ethan-1-ol→(diethoxyphosphoryl)methyl 4-methylbenzenesulfonate→diethyl ((2-(6-amino-9H-purin-9-yl)ethoxy)methyl)phosphonate
Adefovir DipivoxilOptimised routesteps: 2total yield: /
((2-(6-amino-9H-purin-9-yl)ethoxy)methyl)phosphonic acid→chloromethyl pivalate→9H-purin-6-amine→diethyl ((2-chloroethoxy)methyl)phosphonate
Vidarabine MonophosphateOptimised routesteps: 2total yield: /
1-((2R,3S,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione→(1xi)-1,4-Anhydro-1-phosphono-D-arabinitol→6-Aminopurine
Vidarabine MonophosphateOptimised routesteps: 1total yield: /
6-Aminopurine→[(2R,3S,4S,5R)-3,4,5,6-Tetrahydroxyoxan-2-yl]methyl phosphate

Intermediates available on this site

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