712-00-5

Usage

Uses

Used in Pharmaceutical Industry:
9-(2-Hydroxypropyl)adenine is used as an intermediate in the synthesis of isotope labeled analogs for [application reason] the development of anti-HIV and antiviral agents. Its role in the synthesis of rac Tenofovir-13C5 highlights its importance in creating effective treatments for viral infections.
Used in Antiviral Applications:
9-(2-Hydroxypropyl)adenine is used as an anti-HIV agent for [application reason] its ability to inhibit the replication of the HIV virus, thus helping to control the progression of the disease in infected individuals.
Used in Research and Development:
9-(2-Hydroxypropyl)adenine is used as a research compound for [application reason] studying the mechanisms of action and potential applications of acyclic phosphonate nucleotide analogues and reverse transcriptase inhibitors in the field of virology and drug development.

Upstream product

• 108-32-7 1,2-propylene cyclic carbonate 
• 66224-66-6 adenine 
• 73-24-5 7H-purin-6-ylamine 
• 16606-55-6 (R)-1,2-propylene carbonate 
• 4121-40-8 9-propenyladenine 
• 6034-68-0 N⁶-acetyladenine 
• 105970-02-3 1-(6-amino-9H-purin-9-yl)propan-2-one 
• 17435-30-2 (R)-1-(5-Amino-6-chloro-pyrimidin-4-ylamino)-propan-2-ol 
• 180587-74-0 (R)-1-(6-chloro-9H-purin-9-yl) propan-2-ol 
• 160616-02-4 (R)-9-<2-(2-tetrahydropyranyloxy)propyl>adenine 
• 160707-13-1 (S)-9-<2-(2-tetrahydropyranyloxy)propyl>adenine 
• 19686-73-8 1-bromo-2-propanol 
• 101967-10-6 Benzoic acid 2-(6-amino-purin-9-yl)-1-methyl-ethyl ester 
• 852954-49-5 (R)-5-amino-1-(2-hydroxypropyl)-1H-imidazole-4-carbonitrile 

Downstream Products

• 160616-43-3 (S)-9-(2-hydroxypropyl)-N⁶-benzoyladenine 
• 160616-03-5 (R)-9-(2-hydroxypropyl)-N⁶-benzoyladenine 
• 147127-19-3 (S)-9-(2-phosphonylmethoxypropyl)adenine 
• 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 
• 1354647-85-0 (R)-9-[2-(pivaloyloxymethyl)-(isopropoxycarbonyloxymethyl)phosphonoylmethoxypropyl]adenine p-toluenesulfonate 

Relevant academic research and scientific papers

An Efficient Synthesis of Tenofovir (PMPA): A Key Intermediate Leading to Tenofovir-Based HIV Medicines

Herein, we report further improvements to the synthesis of tenofovir 1, the precursor to tenofovir disoproxil fumarate (TDF) and tenofovir alafenamide fumarate (TAF). Starting from acyclic precursor diaminomalononitrile 12, a four-step protocol to tenofovir 1 will allow for vertical integration for more manufacturers. The key transformation is a convergent one-step procedure from 6 as compared to the current commercial process, with an improved yield from 59% (two steps) to 70%. Further improvements include eliminating the need for problematic magnesium tert-butoxide (MTB) and significant solvent reduction by avoiding an intermediate workup. With the costs of HIV/AIDS treatments remaining a barrier for those most in need, lowering the raw material/processing costs and increasing the security of supply can increase patient access.

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.

Tenofovir disoproxil fumarate analog preparation method

The present invention discloses a tenofovir disoproxil fumarate analog preparation method, which comprises: carrying out a substitution reaction on adenine as a raw material and (R)-propylene carbonate in the presence of an alkali, carrying out a substitution reaction with (diethoxyphosphoryl)methyl-4-methylbenzenesulfonate, hydrolyzing with a concentrated hydrochloric acid solution, crystallizingto obtain anhydrous tenofovir, carrying out a reaction on the anhydrous tenofovir and chloromethyl isopropyl carbonate to obtain tenofovir monoester, and carrying out a reaction with 2-bromopropane to obtain the target compound. According to the present invention, the selected starting raw materials are inexpensive and easy to obtain, the process is simple, and the material utilization rate and total yield are improved; and the intermediate of the method is purified by re-crystallization, such that the yield is high, and the purity is high.

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.

Preparation method for tenofovir

The invention relates to the field of chemical synthesis, and in particular relates to a preparation method for tenofovir. The compound provided by the invention has a structure shown by a formula XIIin the description. The method for preparing the tenofovir based on a compound provided by the invention has the advantages that raw materials are cheap and easy to obtain, the process route is short, the conditions are mild and reliable, and the method is easily used for industrialized production.

Preparation method of high-purity tenofovir

The invention provides a preparation method of high-purity tenofovir. The method at least comprises the following steps: (1) preparing R-propylene carbonate; (2) purifying a catalyst; (3) carrying outcondensation reaction on adenine with R-propylene carbonate; (4) carrying out etherification reaction on 9-(2-hydroxypropyl) adenine with diethyl p-toluenesulfonyloxymethylphosphonate; (5) carrying out hydrolysis reaction on tenofovir diester; and (6) refining crude tenofovir.

(R)- (+) - 9 - (2 - hydroxypropyl) adenine preparation method

The invention discloses a preparation method of (R)-(+)-9-(2-hydroxypropyl) adenine, which is a key intermediate for tenofovir disoproxil fumarate. The method comprises the following steps: (1) reacting 6-chloropurine and bromopropanone to obtain 6-chloro-9-(acetonyl)-purine; (2) performing an asymmetric hydrogenation reduction reaction of the resultant 6-chloro-9-(acetonyl)-purine to obtain (R)-(+)-6-chloro-9-(2-hydroxypropyl) adenine; and (3) performing an aminolysis reaction of the resultant (R)-(+)-6-chloro-9-(2-hydroxypropyl) adenine to obtain (R)-(+)-9-(2-hydroxypropyl) adenine. An achiral compound, cheap and easy to obtain, is taken as a raw material in the method; the reaction steps are small; the reaction is easy to deal with; the enantioselectivity of the product is high; and the yield is high, and thus the preparation method has industrialization value.

Preparation method of tenofovir intermediate

The invention discloses a preparation method of a tenofovir intermediate. The preparation method comprises the following steps: 1, contacting and reacting adenine with (Z)-1-halopropylene in an organic solvent in the presence of hexamethylphosphoramide to obtain (Z)-9-propenyladenine; and 2, reacting the (Z)-9-propenyladenine with metachloroperbenzoic acid under the catalysis of a chiral catalyst to obtain the tenofovir intermediate (R)-9-(2-hydroxypropyl)adenine, wherein the chiral catalyst is D-(-)-tartaric acid. The raw materials of the preparation method of the tenofovir intermediate are easy to obtain, so cost control is facilitated; the target product is obtained through introducing relative configuration Z shape alkene and carrying out selective oxidation without using a large amount of a chiral compound, so the product selectivity is good, and the yield is high; and the method has the advantages of no special strict conditions, mild reaction conditions, and convenience in amplified production operation and industrial application promotion.

A method of synthesis for fuwei intermediates (by machine translation)

The invention discloses a method for synthesizing for fuwei intermediate of the method, the method comprises: formula 2 compound of formula 9 - propenyl adenine as raw materials, in the (S)- (-) - 2, 2 '- double (b benzene phosphine base) - 1, 1' - binaphthyl induction, and tetramethyl piperidine nitrogen oxide oxidation reaction to obtain the type 1 indicated by the tenofovir intermediate (R)- 9 - (2 - hydroxy-propyl) adenine; Through the method of the invention for the preparation of tenofovir intermediate (R)- 9 - (2 - hydroxy-propyl) adenine, mild reaction conditions, the industrial application and popularization; yield of the object product, good selectivity; without using a large amount of chiral compounds, the use of a small amount of chiral auxiliary can be induced oxidation, the cost is low. (by machine translation)