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

HRID 1094704Notes

Reaction equation

HRID 1094704 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+].[C:22]([NH:26][C:27](=[O:30])[CH2:28]Cl)([CH3:25])([CH3:24])[CH3:23]>CC#N>[C:22]([NH:26][C:27](=[O:30])[CH2:28][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)([CH3:25])([CH3:24])[CH3:23]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 222440N-tert-butyl-2-chloroacetamideHCID 725279Methyl 5-methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-6-carboxylate

Product 1

HCID 59842876Methyl 3-(2-(tert-butylamino)-2-oxoethyl)-5-methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-6-carboxylate

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 (2.69 g, 12 mmol) in CH3CN (30 mL) was added K2CO3 (2.01 g, 14.5 mmol), KI (2.0 g, 12 mmol), and N-tert-butyl-2-chloroacetamide (1.8 g, 12 mmol). The reaction mixture was refluxed overnight and quenched with H2O (150 mL). The resulting precipitate was filtered and dried to afford methyl 3-(2-(tert-butylamino)-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 (150 mL)
  3. filtrationThe resulting precipitate was filtered
  4. customdried

Sources & evidence

ORD record
ord-5e4fa6b5758549dd9c5fc5155b7d8aea
Source dataset
uspto-grants-2012_03
Patent number
US08133998B2

Reaction notes

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