Methylamine → 2-{3-[cyclopropyl(methyl)amino]-8-thia-4,6-diazatricyclo[7.4.0.0^{2,7}]trideca-1(9),2,4,6-tetraen-5-yl}-N-methylacetamide
Reaction equation
[CH:1]1([N:4]([CH3:24])[C:5]2[C:6]3[C:19]4[CH2:20][CH2:21][CH2:22][CH2:23][C:18]=4[S:17][C:7]=3[N:8]=[C:9]([CH2:11][C:12]([O:14]CC)=O)[N:10]=2)[CH2:3][CH2:2]1.[CH3:25][NH2:26]>C(O)C>[CH:1]1([N:4]([CH3:24])[C:5]2[C:6]3[C:19]4[CH2:20][CH2:21][CH2:22][CH2:23][C:18]=4[S:17][C:7]=3[N:8]=[C:9]([CH2:11][C:12]([NH:26][CH3:25])=[O:14])[N:10]=2)[CH2:3][CH2:2]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
The ethyl 2-(4-(cyclopropyl(methyl)amino)-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-2-yl)acetate (0.6 gm, 0.00173 mol) was dissolved in ethanol (2 ml) in sealed tube. To this 40% aqueous methyl amine (10 ml) was added. The resulting reaction mass was stirred for 18 h at room temperature. After completion of reaction, the solid was collected by filtration. It was washed with ethanol (2 ml) followed by hexane (5 ml) to get crude product. It was purified by column chromatography by using 100-200 mesh silica gel and 1-2% MeOH: DCM as eluent to get 2-(4-(cyclopropyl(methyl)amino)-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-2-yl)-N-methylacetamide as a white solid. Yield—150 mg, (32.82%); 1H-NMR: (400 MHz, CDCl3); δ=8.17 (bs, 1H), 3.84 (s, 2H), 3.06 (s, 3H), 2.88-2.82 (m, 8H), 1.94-1.88 (m, 2H), 1.78-1.72 (m, 2H), 0.80-0.75 (m, 2H), 0.53-0.49 (m, 2H); LC-MS [M+H]=331.0; HPLC purity=99.60%.