Реакция #66684

Уравнение реакции

5-(2,4-Diamino-pyrimidin-5-yloxy)-4-isopropyl-2-methoxy-thiobenzamide

HOAc

NaHCO3

→

5-(2-Isopropyl-4-methoxy-5-thiazol-2-yl-phenoxy)-pyrimidine-2,4-diamine

Выход 28.0%

Условия реакции

Обработка

1. 1
   ЭкстракцияThe aqueous solution was extracted into methylene chloride
2. 2
   ЭкстракцияThe combined organic extract
3. 3
   Сушкаwas dried over Na2SO4
4. 4
   Фильтрацияfiltered
5. 5
   Концентрированиеconcentrated

Методика

To a solution of 5-(2,4-Diamino-pyrimidin-5-yloxy)-4-isopropyl-2-methoxy-thiobenzamide (0.23 g, 0.69 mmol) in HOAc (5 ml) was added bromoactaldehyde diethylacetal (0.18 g, 0.9 mmol) and TsOH (5 mg) as a catalyst. The reaction mixture was heated at 110° C. for 16 hrs and basified with sat. NaHCO3 solution. The aqueous solution was extracted into methylene chloride. The combined organic extract was dried over Na2SO4, filtered and concentrated. Flash chromatography on silica (5% MeOH in methylene chloride with 1% NH4OH) gave 5-(2-Isopropyl-4-methoxy-5-thiazol-2-yl-phenoxy)-pyrimidine-2,4-diamine (0.070 g, 28%) as a yellow solid. (M+H)=358.

Источник