Réaction #554623

Équation de réaction

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

Solvants

dimethylacetamide

Conditions de réaction

Traitement

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

Mode opératoire

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]+.

Source