Benzyl mercaptan → 4-Benzylthio-5-carboxy-2,6-dichloropyrimidine

HRID 917623Notes

Reaction equation

HRID 917623 reaction equation
[C:1]([C:4]1[C:5](Cl)=[N:6][C:7]([Cl:11])=[N:8][C:9]=1[Cl:10])([OH:3])=[O:2].C(N(CC)CC)C.[CH:20]1[CH:25]=[CH:24][C:23]([CH2:26][SH:27])=[CH:22][CH:21]=1>CN(C)C=O.O1CCCC1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[CH2:26]([S:27][C:5]1[C:4]([C:1]([OH:3])=[O:2])=[C:9]([Cl:10])[N:8]=[C:7]([Cl:11])[N:6]=1)[C:23]1[CH:24]=[CH:25][CH:20]=[CH:21][CH:22]=1

Participants

7

Reactant 3

HCID 7509Benzyl mercaptanHCID 8471TriethylamineHCID 200839572,4,6-Trichloropyrimidine-5-carboxylic acid

Product 1

HCID 178482924-Benzylthio-5-carboxy-2,6-dichloropyrimidine

Reagents, catalysts & solvents 3

HCID 311Citric AcidSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 5-carboxy-2,4,6-trichloropyrimidine (prepared in the above (1)) 100 mg, triethylamine 89 mg in dimethylformamide 3 ml is added at room temperature a 1.0M solution of benzylthiol in tetrahydrofuran 0.44 ml, and the mixture is stirred for 1 hour. The reaction mixture is diluted with a 10% aqueous citric acid solution and extracted with ethyl acetate. The organic layer is washed, dried and concentrated in vacuo to give 4-benzylthio-5-carboxy-2,6-dichloropyrimidine as a pale yellow oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer is washed
  3. customdried
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-baa2ccf6fe0d49c3b3cdddb4d97a5c61
Source dataset
uspto-grants-2007_09
Patent number
US07273868B2

Reaction notes

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