Triethylamine → HCID 51348663, compound

Participants

Reaction Steps

4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-5,6-diphenyl-3,4-dihydropyrimidin-2(1H)-one (Compound 1) (400 mg, 0.93 mmol) was dissolved in an EtOH:H2O:THF (8 mL, 2:1:1) mixture. To this was added Zn dust (124 mg, 1.89 mmol) and NH4Cl (104 mg, 1.94 mmol) and stirred at room temperature for 18 hours. After removing a 1 mL aliquot of the reaction mixture, the remaining solution was filtered through a celite pad followed by a solvent swap to DCM/THF (2 mL/2 mL). Et3N (0.1 mL, 0.72 mmol) was added and the solution was stirred for 15 minutes. Mesyl chloride (40 μL, 0.24 mmol) was added and the solution stirred at room temperature for 18 hours. Additional Et3N (0.1 mL, 0.72 mmol) and mesyl chloride (30 μL, 0.18 mmol) was then added and stirred for an additional 6 hours. The crude mixture was concentrated in vacuo and purified by silica-gel column chromatography (0-5% MeOH in EtOAc) to afford 25 mg of Compound 75 as a faint yellow solid. 1H NMR (CD3OD 300 MHz): δ 7.25 (m, 5H), 7.16 (d, 1H), 7.03 (d, 1H), 7.01 (d, 2H), 6.89 (m, 2H), 6.84 (d, 1H), 5.19 (s, 1H), 4.62 (s, 1H), 4.10 (q, 2H), 2.87 (s, 3H), 1.40 (t, 3H); MS (ESI): m/z 480.23 [M+1]+.

Provenance & Evidence