Dimethylformamide → HCID 19801419, compound

HRID 1646144Notes

Reaction equation

HRID 1646144 reaction equation
[CH:1]([O:4][CH:5]([CH3:23])[CH:6](OS(C1C=CC(C)=CC=1)(=O)=O)[C:7]([O:9][CH2:10][CH3:11])=[O:8])([CH3:3])[CH3:2].[CH3:24][O:25][C:26]1[CH:31]=[C:30]([O:32][CH3:33])[N:29]=[C:28]([SH:34])[N:27]=1.CN(C)C=O.C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C.CCCCCC.O>[CH3:33][O:32][C:30]1[CH:31]=[C:26]([O:25][CH3:24])[N:27]=[C:28]([S:34][CH:6]([CH:5]([O:4][CH:1]([CH3:2])[CH3:3])[CH3:23])[C:7]([O:9][CH2:10][CH3:11])=[O:8])[N:29]=1

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 19801422HCID 19801422, compoundHCID 178493561HCID 178493561, compound

Product 1

HCID 19801419HCID 19801419, compoundYield 54.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

After this compound, ethyl 3-(isopropoxy)-2-p-toluenesulfonyloxybutanoate (27.5 g, 0.08 mol) and 4,6-dimethoxy-2-mercaptopyrimidine (13.7 g, 0.08 mol) were added to N,N-dimethylformamide (80 ml) and further anhydrous potassium carbonate (11.1 g) was added thereinto, the mixture was stirred at room temperature for 5 hours. Subsequently, water was added to the reaction mixture, the mixture was extracted with ethyl acetate, washed with water and dried, and ethyl acetate was removed under reduced pressure. The residue obtained was isolated by column chromatography (Wako gel C-200 (trade name, produced by Wako Junyaku K.K.), eluted by hexane:ethyl acetate=8:1) to obtain 15.0 g (yield: 54.5%) of the title compound as a colorless oily product.

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with ethyl acetate
  3. washwashed with water
  4. customdried
  5. customethyl acetate was removed under reduced pressure
  6. customThe residue obtained

Sources & evidence

ORD record
ord-0f739d32d51b49bb95d7d15ae8b2b7eb
Source dataset
uspto-grants-1993_01
Patent number
US05178663

Reaction notes

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