Dimethylformamide → methyl 3-(1,5-dimethyl-2,4-dioxo-1,2-dihydrothieno[2,3-d]pyrimidin-3(4H)-yl)propanoate

HRID 63910Notes

Reaction equation

HRID 63910 reaction equation
[CH3:1][C:2]1[C:10]2[C:9](=[O:11])[N:8]([CH2:12][CH2:13][C:14]([OH:16])=[O:15])C(=O)NC=2[S:4][CH:3]=1.CI.[C:20]([O-])([O-])=O.[K+].[K+].[CH3:26][N:27]([CH:29]=[O:30])[CH3:28]>CC(=O)OCC.O>[CH3:26][N:27]1[C:28]2[S:4][CH:3]=[C:2]([CH3:1])[C:10]=2[C:9](=[O:11])[N:8]([CH2:12][CH2:13][C:14]([O:16][CH3:20])=[O:15])[C:29]1=[O:30]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 118863135HCID 118863135, compound

Product 1

HCID 118863105methyl 3-(1,5-dimethyl-2,4-dioxo-1,2-dihydrothieno[2,3-d]pyrimidin-3(4H)-yl)propanoateYield 63.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 3-(5-methyl-2,4-dioxo-1,2-dihydrothieno[2,3-d]pyrimidin-3(4H)-yl)propanoic acid (330 mg, 1.17 mmol) in DMF (6 mL) was added CH3I (332 mg, 2.33 mmol) followed by K2CO3 (322 mg, 2.33 mmol). The reaction was heated in a sealed tube at 40° C. for 4 h, cooled to RT then diluted with EA (20 mL) and water (20 mL). The organic layer was washed with brine (10 mL), dried over Na2SO4 and concentrated to a residue which was purified by chromatography eluted with DCM/MeOH (50:1) to give methyl 3-(1,5-dimethyl-2,4-dioxo-1,2-dihydrothieno[2,3-d]pyrimidin-3(4H)-yl)propanoate (210 mg, 63.6% yield) as a yellow solid. LCMS: MH+ 283 and TR=1.253 min.

Workup

  1. temperaturecooled to RT
  2. washThe organic layer was washed with brine (10 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated to a residue which
  5. customwas purified by chromatography
  6. washeluted with DCM/MeOH (50:1)

Sources & evidence

ORD record
ord-87837e89da5e48978a10c102a9746d24
Source dataset
uspto-grants-2016_09
Patent number
US09447114B2

Reaction notes

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