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

HRID 1094700Notes

Reaction equation

HRID 1094700 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+].Cl[CH2:23][C:24]([N:26]([CH2:29][CH3:30])[CH2:27][CH3:28])=[O:25]>CC#N>[CH2:27]([N:26]([CH2:29][CH3:30])[C:24](=[O:25])[CH2:23][N:8]1[C:9](=[O:11])[C:10]2[C:2]([CH3:1])=[C:3]([C:12]([O:14][CH3:15])=[O:13])[S:4][C:5]=2[N:6]=[CH:7]1)[CH3:28]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 16844Chloro-N,N-diethylacetamideHCID 725279Methyl 5-methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-6-carboxylate

Product 1

HCID 1680569Methyl 3-(2-(diethylamino)-2-oxoethyl)-5-methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-6-carboxylateYield 97.8%

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 (2.24 g, 10 mmol) in CH3CN (20 mL) was added K2CO3 (1.38 g, 10 mmol), KI (1.61 g, 10 mmol), and 2-chloro-N,N-diethylacetamide (1.4 mL, 10 mmol). The reaction mixture was refluxed overnight and quenched with H2O (50 mL). The resulting precipitate was filtered and dried to afford 3.3 g of methyl 3-(2-(diethylamino)-2-oxoethyl)-5-methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-6-carboxylate as a solid (yield: quantitative).

Workup

  1. temperatureThe reaction mixture was refluxed overnight
  2. customquenched with H2O (50 mL)
  3. filtrationThe resulting precipitate was filtered
  4. customdried

Sources & evidence

ORD record
ord-a5776b74abc7461e8678d9a30a5ac348
Source dataset
uspto-grants-2012_03
Patent number
US08133998B2

Reaction notes

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