Ethyl cyanoacetate → 5-(2-phenylquinolin-7-yl)-3H-thieno[2,3-d]pyrimidin-4-one

반응식

[C:1]1([C:7]2[CH:16]=[CH:15][C:14]3[C:9](=[CH:10][C:11]([C:17]4[C:25]5[C:24](N)=[N:23][CH:22]=[N:21][C:20]=5[S:19][CH:18]=4)=[CH:12][CH:13]=3)[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(C2C=CC3C(=CC(C(=[O:45])C)=CC=3)N=2)C=CC=CC=1.C(CC(OCC)=O)#N>>[C:1]1([C:7]2[CH:16]=[CH:15][C:14]3[C:9](=[CH:10][C:11]([C:17]4[C:25]5[C:24](=[O:45])[NH:23][CH:22]=[N:21][C:20]=5[S:19][CH:18]=4)=[CH:12][CH:13]=3)[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

참가 물질

반응물 3

HCID 7764Ethyl cyanoacetate

HCID 160687065-(2-Phenylquinolin-7-yl)-thieno[2,3-d]pyrimidin-4-ylamine

HCID 577623961-(2-Phenylquinolin-7-yl)-ethanone

생성물 1

HCID 577623885-(2-phenylquinolin-7-yl)-3H-thieno[2,3-d]pyrimidin-4-one

실험 절차

Following the procedure for the one-pot synthesis of 5-(2-phenylquinolin-7-yl)-thieno[2,3-d]pyrimidin-4-ylamine from 1-(2-phenylquinolin-7-yl)-ethanone, but using ethyl cyanoacetate instead of malononitrile, the title compound was obtained as brown solid. 1H NMR (CDCl3, 400 MHz): δ=7.38 (s, 1H), 7.45-7.56 (m, 3H), 7.76-7.79 (dd, 1H, J=1.6 & 8.4 Hz), 7.86-7.91 (m, 2H), 7.98 (s, 1H), 8.15-8.18 (m, 2H), 8.25-8.27 (d, 1H, J=8.8 Hz), 8.34 (d, 1H, J=2.0 Hz). MS (ES+): 356.2 [MH+]. HPLC: tR=4.3 min (MicromassZQ, polar—15 min).