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Methyl 5-bromo-2-(tert-butyl)pyrimidine-4-carboxylate synthesis

1synthesis methods
59950-52-6 Synthesis
5-broMo-2-tert-butyl-pyriMidine-4-carboxylic acid

59950-52-6
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Methyl 5-bromo-2-(tert-butyl)pyrimidine-4-carboxylate

746671-54-5
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Yield:746671-54-5 81%

Reaction Conditions:

in methanol;hexane;benzene; for 48 h;

Steps:

D5.1

A 2.0 M hexanes solution of trimethylsilyldiazomethane (11.8 mL, 23.62 mMol) was added dropwise to a stirring solution of 5-bromo-2-tert-butyl-pyrimidine-4-carboxylic acid (6.12 g, 23.62 mMol) in 9:1 benzene/methanol (100 mL), and the reaction was stirred for 2 days. TLC analysis showed that the reaction was complete, so the mixture was concentrated in-vacuo. The residue was dissolved in ethyl acetate (100 mL), washed with water (3*20 mL), dried over sodium sulfate, then concentrated in-vacuo. Purified over silica gel, eluding with 10% ethyl acetate/hexanes, to yield 5.2 g of a colorless oil as product. MS (ES+)=273,275 (M+H)+. Yield=81%.

References:

US2005/54627,2005,A1 Location in patent:Page/Page column 42