Sodium hydride → HCID 63867703, compound

Participants

Reaction Steps

To a solution of 3-(dimethylamino)-1-propanol (47, 3.45 mL, 2.84 mmol) in 10 mL of dry tetrahydrofuran, sodium hydride (0.0784 g, 3.10 mmol) was added at room temperature. After 15 minutes, 5-bromo-2-chloro-pyrimidine (46, 0.500 g, 2.58 mmol) was added and the mixture was stirred at room temperature for 16 hours. To this, ˜500 μL of saturated ammonium chloride was added and the reaction was treated with ethyl acetate and filtered. The solvents were removed from the filtrate under vacuum, then added diethyl ether, removed solvent under vacuum and repeated twice. The resulting residue was taken up with tetrahydrofuran/acetonitrile and filtered. Silica gel was added to the filtrate and solvents removed under vacuum, then purified by silica gel chromatography eluting with 1 to 6% methanol in dichloromethane, followed with 20% methanol in dichloromethane. The appropriate fractions were combined and the solvents removed under vacuum to provide the desired compound (48, 259 mg). MS (ESI) [M+H+]+=261.9.

Provenance & Evidence