m-Tolylisothiocyanate → Thienopyrimidine deriv. 65
Reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:15]([NH2:17])=[N:14][CH:13]=[N:12][C:11]=3[S:10][C:9]=2[CH3:18])=[CH:4][CH:3]=1.[CH3:19][C:20]1[CH:21]=[C:22]([N:26]=[C:27]=[S:28])[CH:23]=[CH:24][CH:25]=1>CN(C=O)C>[NH2:17][C:15]1[C:16]2[C:8]([C:5]3[CH:4]=[CH:3][C:2]([NH:1][C:27]([NH:26][C:22]4[CH:23]=[CH:24][CH:25]=[C:20]([CH3:19])[CH:21]=4)=[S:28])=[CH:7][CH:6]=3)=[C:9]([CH3:18])[S:10][C:11]=2[N:12]=[CH:13][N:14]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of Example 1E (60 mg, 0.23 mmol) and 3-methylphenyl isothiocyanate in DMF (2 mL) was stirred at room temperature, for 48 hours, quenched with water, and filtered. The filter cake was dried to provide the desired product (75 mg, 80%). MS(ESI(+)) m/e 406 (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ 9.96 (s, 1H); 9.84 (s, 1H); 8.27 (s, 1H); 7.65 (d, J=8.4 Hz, 2H); 7.35 (d, J=8.4 Hz, 2H); 7.30-7.18 (m, 3H); 6.97 (d, J=6.9 Hz, 1H); 2.30 (s, 6H).