Water → HCID 67353995, compound

Participants

Reaction Steps

To a stirred solution containing 1.62 g (7.46 mmol) of 2-(2,5-dimethyl-1H-pyrrol-1-yl)-5-hydroxy-4,6-dimethylpyrimidine (5) in 30 mL of anhydrous THF were added 440 mg (11.00 mmol) of 60% sodium hydride suspension in mineral oil followed by 1.20 mL (10.10 mmol) of benzyl bromide. The reaction mixture was stirred at room temperature under argon atmosphere for 48 h. The reaction mixture was poured into 150 mL of water and extracted with two portions of 100 mL of ethyl acetate. The combined organic solution was washed with a portion of 100 of brine, dried (MgSO4) and then concentrated under diminished pressure. The residue was purified by chromatography on a silica gel column. Elution with hexanes-ethyl acetate 4:1 gave the expected product as light yellow oil: yield 2.20 g (96%). 1H-NMR (CDCl3) δ 7.42 (m, 5H), 5.86 (s, 2H), 4.92 (s, 2H), 2.47 (s, 6H), 2.29 (s, 6H); 13C-NMR (CDCl3) δ 161.59, 152.34, 147.66, 136.05, 129.16, 128.59, 128.26, 107.90, 75.29, 19.10, 14.10.

Provenance & Evidence