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

HRID 1094719Notes

Reaction equation

HRID 1094719 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH2:13][CH2:12][N:11]([C:14]([C:16]2[S:25][C:19]3[N:20]=[CH:21][NH:22][C:23](=[O:24])[C:18]=3[C:17]=2[CH3:26])=[O:15])[CH2:10][CH2:9]1.C([O-])([O-])=O.[K+].[K+].Cl[CH2:34][C:35]([NH:37][C:38]1[CH:43]=[CH:42][C:41]([F:44])=[CH:40][C:39]=1[F:45])=[O:36]>CC#N>[F:45][C:39]1[CH:40]=[C:41]([F:44])[CH:42]=[CH:43][C:38]=1[NH:37][C:35](=[O:36])[CH2:34][N:22]1[C:23](=[O:24])[C:18]2[C:17]([CH3:26])=[C:16]([C:14]([N:11]3[CH2:10][CH2:9][N:8]([C:3]4[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=4[F:1])[CH2:13][CH2:12]3)=[O:15])[S:25][C:19]=2[N:20]=[CH:21]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 7358542-chloro-N-(2,4-difluorophenyl)acetamideHCID 160032576-(4-(2-fluorophenyl)piperazine-1-carbonyl)-5-methylthieno[2,3-d]pyrimidin-4(3H)-one

Product 1

HCID 59842858N-(2,4-difluorophenyl)-2-(6-(4-(2-fluorophenyl)piperazine-1-carbonyl)-5-methyl-4-oxothieno[2,3-d]pyrimidin-3(4H)-yl)acetamideYield 35%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
130 °C

Procedure

To a suspension of 6-(4-(2-fluorophenyl)piperazine-1-carbonyl)-5-methylthieno[2,3-d]pyrimidin-4(3H)-one, (0.06 g, 0.16 mmol) in CH3CN (0.5 mL) was added K2CO3 (22 mg, 0.16 mmol), KI (29 mg, 0.17 mmol), and 2-chloro-N-(2,4-difluorophenyl)acetamide, (36 mg, 0.16 mmol). The reaction mixture was heated at 130° C. for 25 min in a microwave reactor. The reaction was quenched with H2O (25 mL) and the aqueous layer was extracted with EtOAc (25 mL). The organic layer was washed with brine (25 mL), dried over Na2SO4 and concentrated. The crude material was purified by flash chromatography (Et2O:DCM, 1:1) providing 30 mg of pure N-(2,4-difluorophenyl)-2-(6-(4-(2-fluorophenyl)piperazine-1-carbonyl)-5-methyl-4-oxothieno[2,3-d]pyrimidin-3(4H)-yl)acetamide, (yield: 35%).

Workup

  1. customThe reaction was quenched with H2O (25 mL)
  2. extractionthe aqueous layer was extracted with EtOAc (25 mL)
  3. washThe organic layer was washed with brine (25 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe crude material was purified by flash chromatography (Et2O:DCM, 1:1)

Sources & evidence

ORD record
ord-f2bb043b49d941cb8cb86831a0ad4fec
Source dataset
uspto-grants-2012_03
Patent number
US08133998B2

Reaction notes

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