712-00-5

Basic information

• Product Name: 9-(2-hydroxypropyl)adenine
• Synonyms: 9-(2-hydroxypropyl)adenine;1-(6-Amino-9H-purine-9-yl)propane-2-ol;6-Amino-α-methyl-9H-purine-9-ethanol;α-Methyl-6-amino-9H-purine-9-ethanol
• CAS NO: 712-00-5
• Molecular Weight: 0
• Mol File: 712-00-5.mol
• Article Data: 42

Chemical Properties

• Appearance: /
• Solubility: Dichloromethane; Methanol; DMSO
• CAS DataBase Reference: 9-(2-hydroxypropyl)adenine(CAS DataBase Reference)
• NIST Chemistry Reference: 9-(2-hydroxypropyl)adenine(712-00-5)
• EPA Substance Registry System: 9-(2-hydroxypropyl)adenine(712-00-5)

Safety Data

• Hazardous Substances Data: 712-00-5(Hazardous Substances Data)

Usage

Uses

9-(2-Hydroxypropyl)adenine is the unlabeled form of 9-(2-Hydroxypropyl)adenine-13C5 (H952012), which is an intermediate used in the synthesis of rac Tenofovir-13C5 (>90%) (T018501), the isotope labelled analog of Tenofovir (T018500); an acyclic phosphonate nucleotide analogue and reverse transcriptase inhibitor. Also used as an anti-HIV agent and antiviral.

Upstream product

• 101967-10-6 Benzoic acid 2-(6-amino-purin-9-yl)-1-methyl-ethyl ester 
• 19686-73-8 1-bromo-2-propanol 
• 66224-66-6 adenine 
• 108-32-7 1,2-propylene cyclic carbonate 
• 160707-13-1 (S)-9-<2-(2-tetrahydropyranyloxy)propyl>adenine 
• 16606-55-6 (R)-1,2-propylene carbonate 
• 105970-02-3 1-(6-amino-9H-purin-9-yl)propan-2-one 
• 4121-40-8 9-propenyladenine 
• 6034-68-0 N⁶-acetyladenine 
• 160616-02-4 (R)-9-<2-(2-tetrahydropyranyloxy)propyl>adenine 
• 180587-74-0 (R)-1-(6-chloro-9H-purin-9-yl) propan-2-ol 
• 17435-30-2 (R)-1-(5-Amino-6-chloro-pyrimidin-4-ylamino)-propan-2-ol 
• 73-24-5 7H-purin-6-ylamine 
• 15448-47-2 (R)-propylene oxide 

Downstream Products

• 160616-43-3 (S)-9-(2-hydroxypropyl)-N⁶-benzoyladenine 
• 160616-03-5 (R)-9-(2-hydroxypropyl)-N⁶-benzoyladenine 
• 1354647-85-0 (R)-9-[2-(pivaloyloxymethyl)-(isopropoxycarbonyloxymethyl)phosphonoylmethoxypropyl]adenine p-toluenesulfonate 
• 1246812-40-7 propan-2-yl {[(propan-2-yloxy)carbonyl]oxy}methyl {[(2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy}methanephosphonate 
• 147127-19-3 (S)-9-(2-phosphonylmethoxypropyl)adenine 

Relevant articles and documents

Synthesis process of antiviral drug

The invention discloses a synthesis process of an antiviral drug. The process comprises the following steps: reacting adenine (II) with (R)- propylene carbonate (III) to prepare a compound IV, carrying out alkylation reaction on the compound IV and a compound V to prepare a compound VI, and carrying out esterolysis reaction to prepare a compound VII; and carrying out esterification reaction on theprepared compound VII and chloromethyl isopropyl carbonate, and salifying with fumaric acid to prepare the final product tenofovir disoproxil fumarate (I). The synthetic route is simple, the reactionconditions are mild, the generation of impurities is reduced, the total yield and purity of the product are improved, and the method is suitable for industrial production.

Method of preparing tenofovir by using microreactor

The invention provides a method of preparing tenofovir by using a microreactor. The method comprises the following steps: performing a condensation reaction by using adenine and (R)-propylene carbonate as raw materials to prepare (R)-9-(2-hydroxypropyl)adenine, and performing a condensation reaction on the (R)-9-(2-hydroxypropyl)adenine and diethyl(tosyloxy)phosphonate under the action of magnesium tert-butoxide to prepare (R)-9-[2-(diethylphosphonomethoxy)propyl]adenine; and performing a deesterification reaction by adopting a microreactor and using a hydrogen chloride gas as a deesterification reagent to prepare the tenofovir. According to the method provided by the invention, the deesterification reaction uses the hydrogen chloride as the deesterification reagent, and the hydrogen chloride used in the method has a low price and low costs; the quantitative reaction is used, and the deesterification reaction is carried out by using the microreactor technology, so that the reaction pressure and temperature are improved, and the mixing effect is enhanced; the generation amount of waste liquid is less, and the method is green and environmentally friendly; and the method has a fast reaction speed, high reaction efficiency, less side reactions, and high purity and a high yield of the target product, and facilitates industrial production.

Method for preparing tenofovir disoproxil

The invention discloses a method for preparing tenofovir disoproxil and relates to the field of preparation of tenofovir disoproxil. The method for preparing the tenofovir disoproxil specifically comprises the following steps: A) preparing (R)-9-(2-hydroxypropyl) adenine; B) preparing (R)-9-(2-phosphonic acid methoxy-propyl) adenine di(ethyl) ester; C) preparing tenofovir; D) preparing tenofovir disoproxil; and E) carrying out finished product detection and inspection. Compared with the prior art, the method has the beneficial effects that while the medicine effect of the tenofovir disoproxilis ensured, the reaction steps are simplified, the yield is increased, the conversion rates of intermediates (R)-9-(2-hydroxypropyl) adenine, (R)-9-(2-phosphonic acid methoxy-propyl) adenine di(ethyl)ester and tenofovir reach 75%, 63.2% and 74.3% respectively, and the total yield of the tenofovir disoproxil is as high as 62.4% finally.