Potassium Carbonate → Methyl 3-(2-(3,5-bis(trifluoromethyl)phenylamino)-2-oxoethyl)-5-methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-6-carboxylate

HRID 1094710Notes

Reaction equation

HRID 1094710 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]([O:14][CH3:15])=[O:13].C([O-])([O-])=O.[K+].[K+].[F:22][C:23]([F:40])([F:39])[C:24]1[CH:25]=[C:26]([NH:34][C:35](=[O:38])[CH2:36]Cl)[CH:27]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:29]=1>CC#N>[F:22][C:23]([F:39])([F:40])[C:24]1[CH:25]=[C:26]([NH:34][C:35](=[O:38])[CH2:36][N:8]2[C:9](=[O:11])[C:10]3[C:2]([CH3:1])=[C:3]([C:12]([O:14][CH3:15])=[O:13])[S:4][C:5]=3[N:6]=[CH:7]2)[CH:27]=[C:28]([C:30]([F:33])([F:31])[F:32])[CH:29]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 725279Methyl 5-methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-6-carboxylateHCID 1800613N-[3,5-Bis(trifluoromethyl)phenyl]-2-chloroacetamide

Product 1

HCID 59842865Methyl 3-(2-(3,5-bis(trifluoromethyl)phenylamino)-2-oxoethyl)-5-methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-6-carboxylateYield 93.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of methyl 5-methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-6-carboxylate (1.62 g, 7.2 mmol) in CH3CN (35 mL) was added K2CO3 (1.0 g, 7.24 mmol), KI (1.2 g, 7.23 mmol), and N-(3,5-bis(trifluoromethyl)phenyl)-2-chloroacetamide 1 (2.2 g, 7.19 mmol). The reaction mixture was refluxed overnight and quenched with H2O (100 mL). The resultant precipitate was filtered and dried to afford 3.33 g of methyl 3-(2-(3,5-bis(trifluoromethyl)phenylamino)-2-oxoethyl)-5-methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-6-carboxylate, as a solid (yield: 90%).

Workup

  1. temperatureThe reaction mixture was refluxed overnight
  2. customquenched with H2O (100 mL)
  3. filtrationThe resultant precipitate was filtered
  4. customdried

Sources & evidence

ORD record
ord-2d65545dbc5d49618fd160356fd469a5
Source dataset
uspto-grants-2012_03
Patent number
US08133998B2

Reaction notes

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