Reaction #60861

Reaction equation

6-(1-cyclopropyl-4-phenyl-1H-imidazol-5-yl)-4-(methylthio)thieno[2,3-d]pyrimidine

Intermediate 71

6-(1-cyclopropyl-4-phenyl-1H-imidazol-5-yl)-4-(methylthio)thieno[2,3-d]pyrimidine

NH3

NH4Cl

→

title compound

Yield 35.0%

6-(1-Cyclopropyl-4-phenyl-1H-imidazol-5-yl)thieno[2,3-d]pyrimidin-4-amine

Yield 35.0%

Solvents

DCM

water

dioxane

Conditions

Workup

1. 1
   ExtractionThe aqueous layer was extracted with DCM
2. 2
   Concentrationthe combined organics were concentrated
3. 3
   OtherThe crude product was purified by flash chromatography on silica eluting with Hex

Procedure

6-(1-cyclopropyl-4-phenyl-1H-imidazol-5-yl)-4-(methylthio)thieno[2,3-d]pyrimidine (Intermediate 71) (25 mg), NH3 (aq. conc) and NH4Cl (sat. aq.) in dioxane (2 mL) were heated under microwave conditions (CEM explorer, 170° C., 4 hours). The reaction mixture was diluted with DCM and water. The aqueous layer was extracted with DCM and then the combined organics were concentrated. The crude product was purified by flash chromatography on silica eluting with Hex:EtOAc (1:1 to 100% EtOAc, then MeOH:EtOAc 95:5) to afford the title compound as a solid (8 mg, 35%);

Source