Potassium Carbonate → 3-(2-(4,4-difluoropiperidin-1-yl)-2-oxoethyl)-5-methyl-6-(4-phenyl piperazine-1 carbonyl)thieno[2,3-d]pyrimidin-4(3H)-one

HRID 1094716Notes

Reaction equation

HRID 1094716 reaction equation
[CH3:1][C:2]1[C:10]2[C:9](=[O:11])[NH:8][CH:7]=[N:6][C:5]=2[S:4][C:3]=1[C:12]([N:14]1[CH2:19][CH2:18][N:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:16][CH2:15]1)=[O:13].C([O-])([O-])=[O:27].[K+].[K+].[F:32][C:33]1([F:43])[CH2:38][CH2:37][N:36]([CH2:39][C:40](Cl)=O)[CH2:35][CH2:34]1>CC#N>[F:32][C:33]1([F:43])[CH2:38][CH2:37][N:36]([C:39](=[O:27])[CH2:40][N:8]2[C:9](=[O:11])[C:10]3[C:2]([CH3:1])=[C:3]([C:12]([N:14]4[CH2:19][CH2:18][N:17]([C:20]5[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=5)[CH2:16][CH2:15]4)=[O:13])[S:4][C:5]=3[N:6]=[CH:7]2)[CH2:35][CH2:34]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 49910945-methyl-6-(4-phenylpiperazine-1-carbonyl)thieno[2,3-d]pyrimidin-4(3H)-oneHCID 598428832-(4,4-Difluoropiperidin-1-yl)acetyl chloride

Product 1

HCID 598428713-(2-(4,4-difluoropiperidin-1-yl)-2-oxoethyl)-5-methyl-6-(4-phenyl piperazine-1 carbonyl)thieno[2,3-d]pyrimidin-4(3H)-oneYield 50%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of 5-methyl-6-(4-phenylpiperazine-1-carbonyl)thieno[2,3-d]pyrimidin-4(3H)-one, (0.4 g, 1.13 mmol) in CH3CN (5 mL) was added K2CO3 (0.156 g, mmol), KI (0.182 g, 1.13 mmol), and 2-(4,4-difluoropiperidin-1-yl)acetyl chloride (0.223 g, 1.13 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 0.29 g of pure 3-(2-(4,4-difluoropiperidin-1-yl)-2-oxoethyl)-5-methyl-6-(4-phenyl piperazine-1 carbonyl)thieno[2,3-d]pyrimidin-4(3H)-one, (yield: 50%).

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-a5725210d94448a9859428cfa32aeb95
Source dataset
uspto-grants-2012_03
Patent number
US08133998B2

Reaction notes

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