Water → Ethyl 4-chloro-6-methyl-2-(methylsulfanyl)pyrimidine-5-carboxylate

HRID 1950775Notes

Reaction equation

HRID 1950775 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7](O)=[N:8][C:9]([S:13][CH3:14])=[N:10][C:11]=1[CH3:12])=[O:5])[CH3:2].C(N(CC)C(C)C)(C)C.O.O=P(Cl)(Cl)[Cl:28]>C(Cl)Cl.C([O-])(O)=O.[Na+]>[Cl:28][C:7]1[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])=[C:11]([CH3:12])[N:10]=[C:9]([S:13][CH3:14])[N:8]=1

Participants

7

Reactant 4

HCID 962WaterHCID 24813Phosphorus oxychlorideHCID 81531DiisopropylethylamineHCID 178469257HCID 178469257, compound

Product 1

HCID 22225416Ethyl 4-chloro-6-methyl-2-(methylsulfanyl)pyrimidine-5-carboxylateYield 96%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A 100 mL round-bottomed flask was charged with ethyl-4-hydroxy-6-methyl-2-(methylthio)pyrimidine-5-carboxylate (6.49 g, 28.4 mmol) in 14 mL POCl3. To the solution was added N,N-diisopropylethylamine (1.2 mL), the reaction mixture was stirred at 80˜90° C. for 2 hours. The mixture was condensed under reduced pressure yielding the dark brown residue. To the residue was added iced water, then diluted with DCM, and saturated aqueous NaHCO3 solution. The separated organic layer was dried over MgSO4. The solvent was removed by a rotavapor providing dark brown oily product (6.76 g, 96%). MS m/z: 246.9 (M+H)+, 248.9 (isotope).

Workup

  1. customcondensed under reduced pressure
  2. customyielding the dark brown residue
  3. dry with materialThe separated organic layer was dried over MgSO4
  4. customThe solvent was removed by a rotavapor

Sources & evidence

ORD record
ord-0b23ae9b857c473f83b36ff18e81ed5e
Source dataset
uspto-grants-2013_03
Patent number
US08404677B2

Reaction notes

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