Benzyl Chloride → HCID 69077541, compound

HRID 388400Notes

Reaction equation

HRID 388400 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-cd49420a4b224be7828f1cfdc8687077
Source dataset
uspto-grants-2013_02
Patent number
US08377944B2

Reaction notes

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