Phosphorus oxychloride → Methyl (4-chloro-6-methyl-2-methylmercapto-5-pyrimidinyl)-acetate

HRID 1682541Notes

Reaction equation

HRID 1682541 reaction equation
O[C:2]1[C:7]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[C:6]([CH3:13])[N:5]=[C:4]([S:14][CH3:15])[N:3]=1.O=P(Cl)(Cl)[Cl:18]>C(N(CC)C1C=CC=CC=1)C>[Cl:18][C:2]1[C:7]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[C:6]([CH3:13])[N:5]=[C:4]([S:14][CH3:15])[N:3]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178499514HCID 178499514, compound

Product 1

HCID 53971641Methyl (4-chloro-6-methyl-2-methylmercapto-5-pyrimidinyl)-acetateYield 72%

Reagents, catalysts & solvents 1

HCID 7061N,N-DiethylanilineSolvent

Procedure

Methyl (4-hydroxy-6-methyl-2-methylmercapto-5-pyrimidinyl)-acetate (4.0 g, 17 mmol) is heated in a mixture of phosphoroxychloride (40 ml) and N,N-diethylaniline (5.5 ml) for 2 hours at 100° C. The excess phosphoroxychloride was removed by evaporation under vacuum and the residue poured into ice-water. Extraction with ethyl acetate, drying and filtration over silicagel gives methyl (4-chloro-6-methyl-2-methylmercapto-5-pyrimidinyl)-acetate as a crystalline solid (3.1 g, 72%), having a m.p. of 88° C.

Workup

  1. customThe excess phosphoroxychloride was removed by evaporation under vacuum
  2. additionthe residue poured into ice-water
  3. extractionExtraction with ethyl acetate
  4. customdrying
  5. filtrationfiltration over silicagel

Sources & evidence

ORD record
ord-65d223cb18d64e4b918d9e9253e15c7b
Source dataset
uspto-grants-1997_06
Patent number
US05635508

Reaction notes

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