반응 #488259

반응 방정식

3-ethoxy-5-formyl-2-hydroxybenzonitrile

Intermediate 51

3-ethoxy-5-formyl-2-hydroxybenzonitrile

1-phenyl-2-(thiophen-3-yl)ethanone

Intermediate 2

1-phenyl-2-(thiophen-3-yl)ethanone

urea

HCl

→

Compound 105

수율 15.4%

3-ethoxy-2-hydroxy-5-(2-oxo-6-phenyl-5-(thiophen-3-yl)-1,2,3,4-tetrahydropyrimidin-4-yl)benzonitrile

수율 15.4%

용매

ethanol

반응 조건

후처리

1. 1
   온도Refluxed for 2 days
2. 2
   기타Solvent removed
3. 3
   기타resulting residue
4. 4
   기타was purified by prep-HPLC (0.1% TFA as additive)

실험 절차

To a solution of 3-ethoxy-5-formyl-2-hydroxybenzonitrile (Intermediate 51) (70 mg, 0.37 mmol), 1-phenyl-2-(thiophen-3-yl)ethanone (Intermediate 2) (50 mg, 0.28 mmol) and urea (71 mg, 1.1 mmol) in 3 mL of ethanol was added 0.2 mL of concentrated HCl. Refluxed for 2 days. Solvent removed and resulting residue was purified by prep-HPLC (0.1% TFA as additive) to give Compound 105 (18 mg, yield 12%). 1H NMR (DMSO-d6 300 MHz): δ 10.33 (s, 1H), 8.70 (s, 1H), 7.51 (s, 1H), 7.37-7.10 (m, 8H), 6.84 (s, 1H), 6.22 (d, J=4.8 Hz, 1H), 5.16 (d, J=2.4 Hz, 1H), 4.07 (q, J=6.9 Hz, 2H), 1.35 (t, J=6.9 Hz, 3H). MS (ESI): m/z 418.0 [M+1]+.

출처