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ChemicalBook CAS DataBase List 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine
3680-69-1

4-Chloro-7H-pyrrolo[2,3-d]pyrimidine synthesis

9synthesis methods
The preparation process of pyrimidine includes the first α -alkylation reaction between diethyl malonate and allyl bromide, and the subsequent cyclization reaction with amidine to obtain a six-membered ring of bislactam. The chlorination of carbonyl with phosphorus oxychloride to obtain dichloro pyrimidine ring, followed by the oxidation of the terminal double bond with potassium osmate hydrate and sodium periodate to obtain the aldehyde group. The final reaction with ammonia water to produce SNAr/cyclization reaction, a five-step reaction, total yield of 45.8% to obtain 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine. 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine
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Yield:3680-69-1 95%

Reaction Conditions:

with chlorine in 1-methyl-pyrrolidin-2-one;toluene at 160 - 180;Temperature;

Steps:

1-3; 1; 2 Small test:

Add 30ml of NMP / toluene mixed solvent with a volume ratio of 1/3 to a 100ml three-necked flask, add 1g of 4-hydroxypyrrolo [2,3-d] pyrimidine at room temperature, add 3ml of 1,2,3-trichloropropane, the gas in the bottle was replaced with chlorine gas, the temperature was increased to 160-180 ° C, and the reaction was stirred and refluxed for 4-5 hours. Negative pressure is used to remove excess solvent to obtain an oil. Start stirring and add 30ml of 0.5mol / L sodium hydroxide solution to the oil. Stir until the oil is dissolved and the solids are precipitated. / L sodium hydroxide solution was washed 3 times to obtain 1.08 g of 4-chloropyrrolopyrimidine product with a yield of 95% and a purity of 99.5%. The hydrogen spectrum and carbon spectrum were in accordance with the product structure.

References:

CN110790768,2020,A Location in patent:Paragraph 0019; 0021-0025; 0029-0040

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