Triethylamine → Ethyl 2-(4-(cyclopropyl(methyl)amino)-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-2-yl)acetate

HRID 1056832Notes

Reaction equation

HRID 1056832 reaction equation
Cl[C:2]1[C:3]2[C:16]3[CH2:17][CH2:18][CH2:19][CH2:20][C:15]=3[S:14][C:4]=2[N:5]=[C:6]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[N:7]=1.[CH3:21][NH:22][CH:23]1[CH2:25][CH2:24]1.C(N(CC)CC)C>CO>[CH:23]1([N:22]([CH3:21])[C:2]2[C:3]3[C:16]4[CH2:17][CH2:18][CH2:19][CH2:20][C:15]=4[S:14][C:4]=3[N:5]=[C:6]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[N:7]=2)[CH2:25][CH2:24]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 4389052HCID 4389052, compoundHCID 11029756N-Methylcyclopropanamine

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The ethyl 2-(4-chloro-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-2-yl)acetate (7.0 g, 0.0225 mol) and N-methyl cyclopropyl amine (4.8 g, 0.0675 mol) was dissolved in methanol (200 ml). To this reaction mixture, triethyl amine (13.66 g, 0.135 mol) was added slowly at room temperature. The resulting reaction mixture was stirred at room temperature for 18 h. After completion of reaction it was concentrated under reduced pressure. The residue was dissolved in DCM (250 ml) and it was washed with water. Aqueous layer was extracted with DCM (250 ml). Organic extracts were combined and washed with brine. Separated organic layer was dried over anhydrous Na2SO4 and concentrated to get crude compound. It was purified by column chromatography by using 100-200 mesh silica gel and 10% EtOAc:hexane as eluent to give ethyl 2-(4-(cyclopropyl(methyl)amino)-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-2-yl)acetate as a yellow solid. Yield—(6 g, 77.12%); 1H-NMR: (400 MHz, CDCl3); δ=4.20-4.10 (q, 2H), 3.88 (s, 2H), 3.1 (s, 3H), 2.90-2.86 (m, 3H), 2.84-2.83 (m, 2H), 1.93-1.87 (m, 2H), 1.77-1.71 (m, 2H), 1.41 (s, 1H), 1.26-1.23 (t, 3H), 0.72-0.68 (m, 2H), 0.45-0.41 (m, 2H); LC-MS [M+H]=345.9.

Workup

  1. customThe resulting reaction mixture
  2. customAfter completion of reaction it
  3. concentrationwas concentrated under reduced pressure
  4. dissolutionThe residue was dissolved in DCM (250 ml)
  5. washit was washed with water
  6. extractionAqueous layer was extracted with DCM (250 ml)
  7. washwashed with brine
  8. dry with materialSeparated organic layer was dried over anhydrous Na2SO4
  9. concentrationconcentrated
  10. customto get crude compound
  11. customIt was purified by column chromatography

Sources & evidence

ORD record
ord-4357461ae7fa471e80df26210b9dacc5
Source dataset
uspto-grants-2016_07
Patent number
US09399647B2

Reaction notes

Loading…