- Preparation method of 2-amino-4, 6-dichloro-5-formamidopyrimidine
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The invention provides a preparation method of 2-amino-4, 6-dichloro5formyl pyrimidine. The preparation method comprises the following steps: by taking malononitrile, formamidine or hydrochloride thereof as initial raw materials, carrying out nitrosation, formylation, cyclization, diazotization, Sandmeyer and reduction reaction to prepare the 2-amino-4, 6-dichloro-5-formamidopyrimidine. The preparation method disclosed by the invention is high in yield and high in product purity.
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Paragraph 0054; 0062; 0067
(2020/12/30)
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- 2-amino-4,6-dichloro-5-formamide pyrimidine synthesis method
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The invention provides a 2-amino-4,6-dichloro-5-formamide pyrimidine synthesis method. According to the method, 2,5-diamido-4,6-dihydroxypyrimidine reacts with N,N-dimethylformamide in the presence of a chloride reagent, then buffer salt solution is added to reaction liquid, a specific pH value is adopted for hydrolysis, and 2-amino-4,6-dichloro-5-formamide pyrimidine is obtained through reaction. By taking a phosphorus-containing chloride and thionyl chloride mixed reagent as the chloride reagent and selecting a specific pH value range in two times of hydrolysis, the yield and purity of the product obtained with the method are high; furthermore, the whole reaction process is conducted in one reaction system, separation of reaction products generated in different steps is avoided, and operation is simplified greatly; besides, reaction condition is easy to control, and industrial production can be conducted conveniently.
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Paragraph 0038; 0040-0042
(2018/02/04)
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- Method for Producing 2-Amino-4,6-Dichloro-5-Formamidopyrimidine
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The invention relates to a method for producing 2-amino-4,6-dichloro-5-formamidopyrimidine from 2,5-diamino-4,6-dihydroxypyrimidine or a salt thereof. According to said method, a) 2,5-diamino-4,6-dihydroxypyrimidine or the salt or tautomer forms thereof are reacted with a chlorination agent and a formamide of formula (I) wherein R1 and R2 independently represent a C1-C4 alkyl radical or —R1-R2— represents —(CH2)n— where n=4-6, or —(CH2)2-0-(CH2)2—, without adding a solvent, at a temperature of between 50 and 130° C., b) the reaction product obtained in step a) is reacted with water at a temperature of between 0 and 100° C., and regulated to a pH value of between 1 and 6 with an inorganic base, and c) the aqueous reaction mixture obtained in step b) is left to react at a temperature of between 70 and 120° C. under hydrolysis to form 2-amino-4,6-dichloor-5-formamidopyrimidine. The inventive method enables satisfactory yields and high levels of purity of the end product to be obtained. As a result of the significantly reduced reaction volumes due to the solvent, auxiliary substances and residual substances saved, and the significantly simplified method, the costs incurred in the production of 2-amino-4,6-dichloro-5-formylaminopyrimidine are significantly reduced.
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- METHOD FOR PRODUCING 2-AMINO-4,6-DICHLORO-5-FORMAMIDOPYRIMIDINE
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The invention relates to a method for producing 2-amino-4,6-dichloro-5-formamidopyrimidine from 2,5-diamino-4,6-dihydroxypyrimidine or a salt thereof. According to said method, a) 2,5-diamino-4,6-dihydroxypyrimidine or the salt or tautomer forms thereof are reacted with a chlorination agent and a formamide of formula (I) wherein R1 and R2 independently represent a C1-C4 alkyl radical or -R1-R2- represents -(CH2)n- where n = 4-6, or -(CH2)2-0-(CH2)2-, without adding a solvent, at a temperature of between 50 and 130 °C, b) the reaction product obtained in step a) is reacted with water at a temperature of between 0 and 100 °C, and regulated to a pH value of between 1 and 6 with an inorganic base, and c) the aqueous reaction mixture obtained in step b) is left to react at a temperature of between 70 and 120 °C under hydrolysis to form 2-amino-4,6-dichloor-5-formamidopyrimidine. The inventive method enables satisfactory yields and high levels of purity of the end product to be obtained. As a result of the significantly reduced reaction volumes due to the solvent, auxiliary substances and residual substances saved, and the significantly simplified method, the costs incurred in the production of 2-amino-4,6-dichloro-5-formylaminopyrimidine are significantly reduced.
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Page/Page column 8-9
(2010/02/13)
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- Process for the preparation of 2,5-diamino-4,6-dihalogenopyrimidinen
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A halogenated hydrocarbon solvent is used in the production of 2,5-diamino-4,6-dihalo-pyrimidines (I) by reaction of 2,5-diamino-4,6-dihydroxy-pyrimidine (II) or its salts with a phosphorus oxyhalide and a quaternary ammonium halide. A halogenated hydrocarbon solvent is used in the production of 2,5-diamino-4,6-dihalo-pyrimidines of formula (I) by reaction of 2,5-diamino-4,6-dihydroxy-pyrimidine of formula (II) or its salts with a phosphorus oxyhalide and a quaternary ammonium halide. X = halo.
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- Process for the preparation of N-(amino-4,6-dihalo-pyrimidine) formamides
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A process for the preparation of N-(amino-4,6-dihalopyrimidine)formamides of the formula: in which X is a halogen atom, starting from 2,5-diamino-4,6-dihalopyrimidine of the formula: in which X has the meaning afore-mentioned, by reaction with formic acid.
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- An efficient, scalable synthesis of the HIV reverse transcriptase inhibitor Ziagen (1592U89)
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Ziagen, (1S, cis)-4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]-2- cyclopentene-1-methanol, was synthesized from (1S,4R)-azabicyclo[2.2.1]hept- 5-en-3-one by efficient processes which bypass problematic steps in earlier routes. 2-Amino-4,6-dichloro-5-formamidopyrimidine is a key intermediate which makes possible an efficient construction of the purine from a chiral cyclopentenyl precursor.
- Daluge, Susan M.,Martin, Michael T.,Sickles, Barry R.,Livingston, Douglas A.
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p. 297 - 327
(2007/10/03)
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- Chloropyrimidine intermediates
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The present invention is related to a process of making of 2,6-diaminopurines wherein the 6-amino group is substituted by R4 and R5, by reacting a compound of formula (VI) STR1 with an excess of amine NHR4 R5.
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- 4,6-dichloropyrimidine and related compounds
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A novel pyrimidine derivative, N-(2-amino-4,6-dichloropyrimidine-5-yl)formamide for use, e.g., in the production of antiviral nucleotide derivatives, can be made by a process involving cyclyzing an aminomalonic ester with guanidine or its salt in the presence of a base to produce 2,5-diamino-4,6-dihydroxypyrimidine or its salt, chlorinating this product with a chlorinating agent in the presence of an amide to produce 4,6-dichloropyrimidine, and reacting the 4,6-dichlororpyrimidine with an aqueous solution of a carboxylic acid to produce the N-(2-amino-4,6-dichloropyrimidine-5-yl)formammide. Novel also are 4,6-dichloropyrimidine, 4,6-dichloro-N'-(dimethylaminomethylene)pyrimidine-2,5-diamine, 4,6-dichloro-N'-(piperidine-1-ylmethylene)pyrimidine-2,5-diamine, and a process for making 2,5-diamino-4,6-dichloropyrimidine.
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