Реакция #554623

Уравнение реакции

Water

NaH

2,2,2-Trifluoro-N-(4-hydroxymethyl-benzyl)-acetamide

2-Chloropyrimidin-4-amine

→

N-(4-((4-Aminopyrimidin-2-yloxy)methyl)benzyl)-2,2,2-trifluoroacetamide

Растворители

dimethylacetamide

Условия реакции

Обработка

1. 1
   Другоеto quench all excess NaH
2. 2
   workup.ADDITIONthe mixture poured into 50 ml of 0.5 N HCl
3. 3
   ЭкстракцияThe crude product is extracted with ethyl acetate
4. 4
   Промывкаthe combined organic phases washed with brine
5. 5
   Сушкаdried over MgSO4
6. 6
   ДругоеAfter evaporation of the solvent
7. 7
   Другоеthe product is purified by flash column chromatography (gradient ethyl acetate:cyclohexane from 1:1 to 3:1)

Методика

760 mg (3.25 mmol) 2,2,2-Trifluoro-N-(4-hydroxymethyl-benzyl)-acetamide is dissolved in 3 mL dry dimethylacetamide under argon atmosphere, and 273 mg (8.15 mmol) NaH is added over 5 min. 211 mg (1.63 mmol) 2-Chloropyrimidin-4-amine is then added and the solution stirred at 90° C. over night. 1 mL Water is added carefully to quench all excess NaH, and the mixture poured into 50 ml of 0.5 N HCl. The crude product is extracted with ethyl acetate, the combined organic phases washed with brine and dried over MgSO4. After evaporation of the solvent, the product is purified by flash column chromatography (gradient ethyl acetate:cyclohexane from 1:1 to 3:1). Yield: 350 mg (52%). ESI-MS m/z 327 [M+H]+.

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