Chloroacetyl chloride → HCID 66823093, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1g (30 mg, 0.068 mmol) and Et3N (0.04 mL, 0.28 mmol) in CH2Cl2 (3 mL) at 0° C. was added chloroacetyl chloride (11.5 mg, 0.10 mmol). The reaction was stirred at 0° C. for 1.5 h, and was then quenched with aq. NaHCO3. The resulting mixture was extracted with CH2Cl2. The organic solution was dried over Na2SO4 and concentrated. The resulting residue was stirred with TFA (0.5 mL) in CH2Cl2 (2 mL) for 1.5 h. The solution was concentrated, and the residue was stirred in aq. NaHCO3 (2 mL) and THF (3 mL) for 24 h. To the resulting intermediate 1h in this mixture of aq. NaHCO3 and THF was added K2CO3 (28 mg, 0.20 mmol) and 2-bromopyrimidine (32 mg, 0.20 mmol). The reaction mixture was heated to reflux for 16 h, and was then extracted with CH2Cl2. The organic solution was dried over Na2SO4 and concentrated. Purification by column chromatography (silica gel, 3% MeOH/CH2Cl2) gave Cpd 23 as a white solid (7 mg). MS 462 (M+H+).

Provenance & Evidence