Sodium hydride → HCID 68041347, compound

Participants

Reaction Steps

To a solution of 4-[(3-chloro-2-methylphenyl)methyl]-2-(4-morpholinyl)-5-thioxo-5,6-dihydro[1,3]thiazolo[4,5-d]pyrimidin-7(4H)-one (Example 107) (150 mg, 0.367 mmol) in N,N-Dimethylformamide (DMF) (2 mL) in a 20 mL Scintillation vial stirred at rt was added sodium hydride (27.8 mg, 1.100 mmol). After stirring at rt for 10 minutes, 1,1-dimethylethyl bromoacetate (0.108 mL, 0.734 mmol) was added and the reaction mixture was capped. Upon addition a precipitate immediately formed and the reaction mixture became a thick almost solid suspension. A portion of the solid was checked by LC/MS and it indicated that the reaction had gone about 80%. The reaction mixture was quenched with saturated NH4Cl solution and diluted with 15 mL water. The yellow-orange solid was isolated by filtration, washed with water and dried in a vacuum oven at 65 C for two hours providing 182 mg of solid that was used without further purification in the next step LC/MS (ES) m/z=524 (M+H).

Provenance & Evidence