Triethylamine → HCID 66826244, compound

Participants

Reaction Steps

4-(4-Hydroxy-3-methoxy-5-nitrophenyl)-5,6-diphenyl-3,4-dihydropyrimidin-2(1H)-one (Compound 9) (100 mg, 0.24 mmol) was dissolved in an EtOH:H2O:THF (4 mL, 2:1:1) mixture. To this was added Zn dust (26 mg, 0.40 mmol) and NH4Cl (26 mg, 0.48 mmol) and stirred at room temperature for 1 day, followed by stirring at 50° C. for 1 day. The solution was filtered through a celite pad followed by a solvent swap to DCM (5 mL). Excess Et3N (0.1 ml, 0.72 mmol) was added and stirred for 15 minutes, followed by excess addition of mesyl chloride (50 μL, 0.3 mmol) and stirring over night. The crude mixture was directly purified by silica-gel column chromatography (0 to 5% MeOH in EtOAc) to yield 10 mg of Compound 76 as a faint yellow solid. 1H NMR (CD3OD 300 MHz): δ 7.27 (m, 5H), 7.06 (m, 1H), 7.04 (d, 2H), 6.91 (m, 2H), 6.61 (d, 1H), 6.38 (d, 1H), 5.51 (s, 1H), 5.14 (s, 1H), 3.77 (s, 3H)); MS (ESI): m/z 466.17 [M+1]+.

Provenance & Evidence