Реакция #2075733

ord-5b8cb3e1963e480f9284bc31dc2ba1d7

Уравнение реакции

COC(=O)c1nc(-c2ccc(Cl)c(OC)c2F)nc(N)c1SC
6-amino-2-(4-chloro-2-fluoro-3-methoxyphenyl)-5-methylsulfanyl-pyrimidine-4-carboxylic acid methyl ester
[Na+].[OH-]
sodium hydroxide
Cl
HCl
COc1c(Cl)ccc(-c2nc(N)c(SC)c(C(=O)O)n2)c1F
title compound
Выход 70.6%
COc1c(Cl)ccc(-c2nc(N)c(SC)c(C(=O)O)n2)c1F
6-Amino-2-(4-chloro-2-fluoro-3-methoxyphenyl)-5-methylsulfanyl-pyrimidine-4-carboxylic acid
Выход 70.6%

Растворители

Условия реакции

Подробные условия
See reaction.notes.procedure_details.

Обработка

  1. 1
    КонцентрированиеThe resulting solution was concentrated
  2. 2
    Другоеpartitioned between ethyl acetate and water
  3. 3
    ДругоеThe organic phase was dried
  4. 4
    Концентрированиеconcentrated

Методика

6-amino-2-(4-chloro-2-fluoro-3-methoxyphenyl)-5-methylsulfanyl-pyrimidine-4-carboxylic acid methyl ester (100 mg, 0.28 mmol) was dissolved in 2 mL methanol and 0.5 mL of 2N sodium hydroxide (1 mmol) was added. The reaction mixture was stirred at room temperature for 4 h and then acidified with a slight excess of 2N HCl. The resulting solution was concentrated and partitioned between ethyl acetate and water. The organic phase was dried and concentrated to yield the title compound (68 mg, 70% yield): mp 153° C. (dec.): 1H NMR (CDCl3): δ 7.63 (m, 1H), 7.2 (m, 1H), 6.4 (br s, 2H), 3.98 (s, 3H), 2.42 (s, 3H).

Источник

DOI: 10.6084/m9.figshare.5104873.v1Патент: US07642220B2uspto-grants-2010_01