Dimethylformamide → HCID 117988910, compound

HRID 2201363Notes

Reaction equation

HRID 2201363 reaction equation
[Na].[CH2:2]([SH:4])[CH3:3].[CH2:5]([O:7][C:8]([C:10]1[C:11](Cl)=[N:12][CH:13]=[N:14][CH:15]=1)=[O:9])[CH3:6].CN(C=O)C.C1COCC1>O>[CH2:5]([O:7][C:8]([C:10]1[C:11]([S:4][CH2:2][CH3:3])=[N:12][CH:13]=[N:14][CH:15]=1)=[O:9])[CH3:6]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8028TetrahydrofuranHCID 12684326Ethyl 4-chloropyrimidine-5-carboxylateHCID 45051917Sodium ethanethiol

Product 1

HCID 117988910HCID 117988910, compoundYield 45.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2.77 g of ethyl mercaptan sodium salt (80%) was added to a mixture of 4.69 g of 4-chloropyrimidine-5-carboxylic acid ethyl ester, 8 ml of DMF and 7 ml of THF was added under ice cooling, then the mixture was heated to room temperature, and stirred for 1 hour. Water was poured to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, then dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was applied to a silica gel column chromatography to obtain 2.41 g of 4-ethylsulfanylpyrimidine-5-carboxylic acid ethyl ester. 4-Ethylsulfanylpyrimidine-5-carboxylic acid ethyl ester

Workup

  1. additionwas added under ice cooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0b34a10d492941f4bb26d120bf8d8dc7
Source dataset
uspto-grants-2016_06
Patent number
US09364000B2

Reaction notes

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