Tetrahydrofuran → 4-Chloro-6-methoxy-2-(methylsulfanyl)pyrimidine-5-carboxylic acid

HRID 917654Notes

Reaction equation

HRID 917654 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([OH:10])=[O:9])=[C:6](Cl)[N:5]=[C:4]([S:12][CH3:13])[N:3]=1.CN(C)[C:16](=[O:18])C.O1CCCC1.[H-].[Na+]>CO>[Cl:1][C:2]1[C:7]([C:8]([OH:10])=[O:9])=[C:6]([O:18][CH3:16])[N:5]=[C:4]([S:12][CH3:13])[N:3]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 31374DimethylacetamideHCID 220535774,6-Dichloro-2-(methylthio)pyrimidine-5-carboxylic acid

Product 1

HCID 178483634-Chloro-6-methoxy-2-(methylsulfanyl)pyrimidine-5-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 4,6-dichloro-5-carboxy-2-methylthiopyrimidine (prepared in Example 320(1)) 5.00 g, N,N-dimethylacetamide 50 ml, tetrahydrofuran 20 ml and sodium hydride (60%) 1.673 g is stirred for 20 minutes on an ice bath. Methanol 5 ml is dropped thereto over a period of 30 minutes and the mixture is stirred for 15 minutes. The reaction mixture is diluted with a 10% aqueous citric solution and extracted with ethyl acetate. The organic layer is washed, dried and concentrated in vacuo. The resulting solid is triturated with hexane in ice to give 4-chloro-5-carboxy-6-methoxy-2-methylthiopyrimidine as a slightly brown crystalline powder, 4.61 g. mp 179-181° C.

Workup

  1. waitover a period of 30 minutes
  2. stirringthe mixture is stirred for 15 minutes
  3. extractionextracted with ethyl acetate
  4. washThe organic layer is washed
  5. customdried
  6. concentrationconcentrated in vacuo
  7. customThe resulting solid is triturated with hexane in ice

Sources & evidence

ORD record
ord-a3f2a16649414dd08766509340d039d2
Source dataset
uspto-grants-2007_09
Patent number
US07273868B2

Reaction notes

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