Sodium hydride → 4,4-dimethyl-3-(1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-1-{4-[(trifluoromethyl)sulfanyl]phenyl}tetrahydropyrimidin-2(1H)-one

Participants

Reaction Steps

To a solution of the 4,4-dimethyl-1-{4-[(trifluoromethyl) sulfanyl]phenyl}tetrahydropyrimidin-2(1H)-one (10 mg, 0.03 mmol) in 2 mL DMF was added NaH (2.4 mg, 0.03 mmol). The mixture was allowed to stir at ambient temperature for 10 min. The reaction was treated with tert-butyl 3-(chloromethyl)-1H-pyrrolo[2,3-b]pyridine-1-carboxylate (8.8 mg, 0.03 mmol) and allowed to stir at ambient temperature for 16 h. The reaction was partitioned between water and ether. The organics were washed with water and brine, then dried over Na2SO4, filtered and concentrated. The residue was purified by silica gel chromatography to give 4,4-dimethyl-3-(1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-1-{4-[(trifluoromethyl)sulfanyl]phenyl}tetrahydropyrimidin-2(1H)-one. 1H NMR (399 MHz, CDCl3): δ 9.05 (s, 1 H); 8.30 (d, J=4.7 Hz, 1 H); 8.11 (d, J=7.9 Hz, 1 H); 7.63 (d, J=8.2 Hz, 2 H); 7.46-7.41 (m, 2 H); 7.36 (s, 1 H); 7.11-7.06 (m, 1 H); 4.80 (s, 2 H); 3.76-3.69 (m, 2H); 2.04-1.97 (m, 2 H); 1.36 (s, 6 H). LCMS [M+H]+=435.3.

Provenance & Evidence