Benzyl Chloride → HCID 69077541, compound

HRID 2066939Notes

Reaction equation

HRID 2066939 reaction equation
[CH3:1][C:2]1[NH:3][C:4](=[O:17])[C:5]2[C:10]([CH3:11])=[C:9]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[S:8][C:6]=2[N:7]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:24](Cl)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C(#N)C>[CH2:24]([N:3]1[C:4](=[O:17])[C:5]2[C:10]([CH3:11])=[C:9]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[S:8][C:6]=2[N:7]=[C:2]1[CH3:1])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 336248ethyl 2,5-dimethyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-6-carboxylate

Product 1

HCID 69077541HCID 69077541, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 252 mg of ethyl 2,5-dimethyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-6-carboxylate, 138 mg of potassium carbonate, 15 mL of acetonitrile and 1 mL of benzyl chloride was heated under reflux overnight. After condensing the reaction mixture under reduced pressure, the residue was purified on silica gel column chromatography (chloroform:methanol=100:1) to provide 153 mg (45%) of the title compound.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux overnight
  3. customAfter condensing the reaction mixture under reduced pressure
  4. customthe residue was purified on silica gel column chromatography (chloroform:methanol=100:1)

Sources & evidence

ORD record
ord-a814d61bb4f34ac1acbff88eaea2098b
Source dataset
uspto-grants-2012_10
Patent number
US08293754B2

Reaction notes

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