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

HRID 1056833Notes

Reaction equation

HRID 1056833 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]1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 89714188Ethyl 2-(4-(cyclopropyl(methyl)amino)-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-2-yl)acetate

Product 1

HCID 897136302-{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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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%.

Workup

  1. customThe resulting reaction mass
  2. customAfter completion of reaction
  3. filtrationthe solid was collected by filtration
  4. washIt was washed with ethanol (2 ml)
  5. customto get crude product
  6. customIt was purified by column chromatography

Sources & evidence

ORD record
ord-0ae8110950e44876a9e85b6cdf9bf8e7
Source dataset
uspto-grants-2016_07
Patent number
US09399647B2

Reaction notes

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