Phosphorus oxychloride → Methyl (4-chloro-6-methylpyrimidin-5-yl)acetate

HRID 1682537Notes

Reaction equation

HRID 1682537 reaction equation
O[C:2]1[C:7]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[C:6]([CH3:13])[N:5]=[CH:4][N:3]=1.P(Cl)(Cl)([Cl:16])=O>C1(C)C=CC=CC=1>[CH3:12][O:11][C:9](=[O:10])[CH2:8][C:7]1[C:2]([Cl:16])=[N:3][CH:4]=[N:5][C:6]=1[CH3:13]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178499509HCID 178499509, compound

Product 1

HCID 10954591Methyl (4-chloro-6-methylpyrimidin-5-yl)acetateYield 82%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A suspension of methyl (4-hydroxy-6-methyl-5-pyrimidinyl)-acetate (116 g, 0.64 mol) in toluene (200 ml) and phosphorous oxychloride (94 ml, 1.0 mol) is refluxed for three hours. The solvent is removed under reduced pressure and the resulting oil is poured onto crushed ice with stirring. The pH is adjusted to 9 by adding potassium carbonate. Extraction with ether, drying and destillation under high vacuum gives methyl(4-chloro-6-methyl-5-pyrimidinyl)-acetate as a yellowish oil (105 g, 82 %). b.p./l torr 88°-91° C.

Workup

  1. temperatureis refluxed for three hours
  2. customThe solvent is removed under reduced pressure
  3. additionthe resulting oil is poured
  4. customonto crushed ice
  5. additionby adding potassium carbonate
  6. extractionExtraction with ether
  7. customdrying

Sources & evidence

ORD record
ord-fcdf28dd5780416eb44a700dc8b2e446
Source dataset
uspto-grants-1997_06
Patent number
US05635508

Reaction notes

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