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

HRID 1094722Notes

Reaction equation

HRID 1094722 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[CH2:18][CH2:17][CH2:16][CH2:15]1)=[O:13].C([O-])([O-])=O.[K+].[K+].Cl[CH2:26][C:27]([N:29]1[CH2:34][CH2:33][N:32]([C:35]2[CH:40]=[CH:39][CH:38]=[C:37]([Cl:41])[CH:36]=2)[CH2:31][CH2:30]1)=[O:28]>CC#N>[Cl:41][C:37]1[CH:36]=[C:35]([N:32]2[CH2:31][CH2:30][N:29]([C:27](=[O:28])[CH2:26][N:8]3[C:9](=[O:11])[C:10]4[C:2]([CH3:1])=[C:3]([C:12]([N:14]5[CH2:18][CH2:17][CH2:16][CH2:15]5)=[O:13])[S:4][C:5]=4[N:6]=[CH:7]3)[CH2:34][CH2:33]2)[CH:40]=[CH:39][CH:38]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 41653802-Chloro-1-(4-(3-chlorophenyl)piperazin-1-yl)ethan-1-oneHCID 598428315-methyl-6-(pyrrolidine-1-carbonyl)thieno[2,3-d]pyrimidin-4(3H)-one

Product 1

HCID 598428403-(2-(4-(3-chlorophenyl)piperazin-1-yl)-2-oxoethyl)-5-methyl-6-(pyrrolidine-1-carbonyl)thieno[2,3-d]pyrimidin-4(3H)-oneYield 22%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of 5-methyl-6-(pyrrolidine-1-carbonyl)thieno[2,3-d]pyrimidin-4(3H)-one, (0.06 g, 0.23 mmol) in CH3CN (5 mL) was added K2CO3 (0.032 g, 0.23 mm (38 mg, 0.23 mmol), and 2-chloro-1-(4-(3-chlorophenyl)piperazin-1-yl)ethanone, (0.062 g, 0.23 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 0.025 g of pure 3-(2-(4-(3-chlorophenyl)piperazin-1-yl)-2-oxoethyl)-5-methyl-6-(pyrrolidine-1-carbonyl)thieno[2,3-d]pyrimidin-4(3H)-one, (yield: 22%).

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-60b8a171ea4141d59a986e7614b5f16d
Source dataset
uspto-grants-2012_03
Patent number
US08133998B2

Reaction notes

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