Реакция #2256508

Уравнение реакции

5-benzyloxy-6-hydroxy-2-(1-phenyl-cyclopentylmethyl)-pyrimidine-4-carboxylic acid

[2-(tert-butyl-dimethylsilanyloxy)-ethyl]-cyclobutyl-amine

[2-(tert-butyl-dimethylsilanyloxy)-ethyl]-cyclopentylamine

N,N-diisopropylethylamine

HATU

→

5-benzyloxy-6-hydroxy-2-(1-phenyl-cyclopentylmethyl)-pyrimidine-4-carboxylic acid [2-(tert-butyl-dimethylsilanyloxy)-ethyl]-cyclobutyl-amide

Выход 92.2%

Растворители

dimethylformamide

water

Условия реакции

Обработка

1. 1
   Экстракцияthe mixture was extracted with ethyl acetate (3×20 mL)
2. 2
   ПромывкаThe combined organic part was washed with water (3×50 mL) and brine (2×30 mL)
3. 3
   Другоеdried
4. 4
   Концентрированиеconcentrated
5. 5
   ДругоеThe crude product was purified by Combi-Flash column (eluted at 20-30% ethyl acetate in hexane)

Методика

To a stirred solution mixture of 5-benzyloxy-6-hydroxy-2-(1-phenyl-cyclopentylmethyl)-pyrimidine-4-carboxylic acid (283) (300 mg, 0.74 mmol) and [2-(tert-butyl-dimethylsilanyloxy)-ethyl]-cyclobutyl-amine (8e) (204 mg, 0.89 mmol) in dimethylformamide (5 mL) were added N,N-diisopropylethylamine (0.4 mL, 2.22 mmol) and HATU (423 mg, 1.11 mmol). After stirring at room temperature for 1 h, water (50 mL) was added and the mixture was extracted with ethyl acetate (3×20 mL). The combined organic part was washed with water (3×50 mL) and brine (2×30 mL) and dried and concentrated. The crude product was purified by Combi-Flash column (eluted at 20-30% ethyl acetate in hexane) to get 5-benzyloxy-6-hydroxy-2-(1-phenyl-cyclopentylmethyl)-pyrimidine-4-carboxylic acid [2-(tert-butyl-dimethylsilanyloxy)-ethyl]-cyclobutyl-amide (292) (420 mg, 91.94%) as a yellow sticky solid.

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