Potassium Carbonate → 2-(6-(4-(3-chlorophenyl)piperazine-1-carbonyl)-5-methyl-4-oxothieno[2,3-d]pyrimidin-3 (4H)-yl)-N-ethyl-N-(2,2,2-trifluoroethyl)acetamide

HRID 1094726Notes

Reaction equation

HRID 1094726 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([C:16]3[S:25][C:19]4[N:20]=[CH:21][NH:22][C:23](=[O:24])[C:18]=4[C:17]=3[CH3:26])=[O:15])[CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.C([O-])([O-])=O.[K+].[K+].Cl[CH2:34][C:35]([N:37]([CH2:43][CH3:44])[CH2:38][C:39]([F:42])([F:41])[F:40])=[O:36]>CC#N>[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([C:16]3[S:25][C:19]4[N:20]=[CH:21][N:22]([CH2:34][C:35]([N:37]([CH2:43][CH3:44])[CH2:38][C:39]([F:40])([F:41])[F:42])=[O:36])[C:23](=[O:24])[C:18]=4[C:17]=3[CH3:26])=[O:15])[CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 41967806-{[4-(3-Chlorophenyl)piperazino]carbonyl}-5-methylthieno[2,3-D]pyrimidin-4(3H)-oneHCID 598428332-chloro-N-ethyl-N-(2,2,2-trifluoroethyl)acetamide

Product 1

HCID 598428602-(6-(4-(3-chlorophenyl)piperazine-1-carbonyl)-5-methyl-4-oxothieno[2,3-d]pyrimidin-3 (4H)-yl)-N-ethyl-N-(2,2,2-trifluoroethyl)acetamideYield 21%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of 6-(4-(3-chlorophenyl)piperazine-1-carbonyl)-5-methylthieno[2,3-d]pyrimidin-4(3H)-one, (0.1 g, 0.26 mmol) in CH3CN (5 mL) was added K2CO3 (36 mg, 0.26 mmol), KI (43 mg, 0.26 mmol), and 2-chloro-N-ethyl-N-(2,2,2-trifluoroethyl)acetamide, (52 mg, 0.26 mmol). The reaction mixture was refluxed overnight and then quenched with H2O (20 mL). The resultant precipitate was filtered and dried to provide a crude solid which was purified by flash chromatography (Et2O:DCM, 1:1) providing 30 mg of pure 2-(6-(4-(3-chlorophenyl)piperazine-1-carbonyl)-5-methyl-4-oxothieno[2,3-d]pyrimidin-3 (4H)-yl)-N-ethyl-N-(2,2,2-trifluoroethyl)acetamide, (yield: 21%).

Workup

  1. temperatureThe reaction mixture was refluxed overnight
  2. customquenched with H2O (20 mL)
  3. filtrationThe resultant precipitate was filtered
  4. customdried
  5. customto provide a crude solid which
  6. customwas purified by flash chromatography (Et2O:DCM, 1:1)

Sources & evidence

ORD record
ord-d09b64ef28a541c09e504d23b351078b
Source dataset
uspto-grants-2012_03
Patent number
US08133998B2

Reaction notes

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