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

• 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 
• 73-24-5 7H-purin-6-ylamine 
• 852954-49-5 (R)-5-amino-1-(2-hydroxypropyl)-1H-imidazole-4-carbonitrile 
• 3473-63-0 formamidine acetic acid 
• 1464851-21-5 (Z)-6-amino-9-(prop-1-en-1-yl)-9H-purine 

Downstream Products

• 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 
• 160616-03-5 (R)-9-(2-hydroxypropyl)-N⁶-benzoyladenine 
• 160616-43-3 (S)-9-(2-hydroxypropyl)-N⁶-benzoyladenine 

Relevant academic research and scientific papers

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.

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.

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 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.

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.

Method of preparing tenofovir

The invention provides a method for preparing tenofovir. The method is characterized by comprising the following steps: 1) reacting 9-(2-hydroxy propyl) adenine with a compound as shown in the formula (1) in the specification in the presence of magnesium alkoxide to prepare tenofovir ethyl ester, wherein Y is selected from methyl, trifluoromethyl, phenyl or 4-trifluoromethylphenyl; 2) hydrolyzing the tenofovir ethyl ester in the presence of a dealkylation reagent to prepare tenofovir. The method for preparing tenofovir provided by the invention has the advantages of safe process, good product quality, high yield and suitability for industrialization.

Synthesis Method For Improved Tenofovir Disoproxil Fumarate Using Ion-Exchange Resin And Method For Preparing Oral Dissolving Film Form Using The Same

The present invention relates to a synthesis method of preventing the formation of impurities and byproducts in the synthesis of tenofovir disoproxil fumarate (Teno-DF) used as a medicine for hepatitis B and HIV treatment due to its function to promote bioactivities. In the synthesis method of the present invention, an ion-exchange resin (Dowex 50W hydrogen form, sulfonic acidic cation exchange resin) is used to enhance the yield and purity of the compound. The present invention also relates to a method of preparing an oral dissolving film dosage form in the manufacture of a medicine using the tenofovir compound with high purity obtained by the synthesis method of the present invention as an effective ingredient.

for Fuwei ester bulk drug and tablet (by machine translation)

The invention relates to a raw material for the fuwei ester and tablet, the states for Fuwei the ester bulk drug preparation method comprises the following steps: compound 1 with R - propylene carbonate reaction, be R - 9 - (2 - hydroxy-propyl) adenine; R - 9 - (2 - hydroxy-propyl) adenine with toluene-sulfonyloxy diethyl phosphoric condensation reaction, generating compound 2 compound 2 hydrolysis to obtain the tenofovir, for fuwei with chloromethyl carbonic acid isopropyl ester condensation to get said states for Fuwei the ester. The states for Fuwei the ester tablet, comprises the following weight percentages of each component: for Fuwei ester bulk drug, microcrystalline cellulose, anhydrous lactose, or microcrystalline cellulose aqueous solution, sodium carboxy methyl cellulose, magnesium stearate. The preparation method of the raw material for the fuwei ester reaction yield is high, and the production process simple and convenient operation, all of the raw materials are cheap and easy to get with low operation difficulty, production risk is low, is conducive to the realization of large-scale industrial production. (by machine translation)