Sodium Hydroxide → HCID 17965790, compound

Reaction equation

[NH2:1][C:2]1[C:3]2[CH:10]=[C:9]([C:11]3[N:15]([CH2:16][CH:17]=O)[CH:14]=[N:13][C:12]=3[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[S:8][C:4]=2[N:5]=[CH:6][N:7]=1.[CH3:25][N:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1.[OH-].[Na+]>CC(O)=O>[CH3:25][N:26]1[CH2:31][CH2:30][N:29]([CH2:17][CH2:16][N:15]2[C:11]([C:9]3[S:8][C:4]4[N:5]=[CH:6][N:7]=[C:2]([NH2:1])[C:3]=4[CH:10]=3)=[C:12]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[N:13]=[CH:14]2)[CH2:28][CH2:27]1

Participants

Procedure

[5-(4-Aminothieno[2,3-d]pyrimidin-6-yl)-4-phenyl-1H-imidazol-1-yl]acetaldehyde (Intermediate 74) (100 mg) and N-methyl piperazine (100 μL) were stirred in AcOH (1 mL) for 15 minutes. Na(AcO)3BH (70 mg) was added and the reaction allowed to stir overnight. The reaction was made basic with 2M NaOH (50 mL) and then the product extracted with DCM (3×50 mL). The organics were washed with water (30 mL), brine (30 mL), dried (MgSO4) and concentrated in vacuo. The product was purified by flash chromatography on silica eluting with DCM:7N NH3 in MeOH. (95:5) to afford the title compound as a solid (32 mg, 28%);