Phosphorus oxychloride → HCID 13060218, compound

HRID 1075263Notes

Reaction equation

HRID 1075263 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6](O)[N:5]=[C:4]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[N:3]=1.P(Cl)(Cl)([Cl:17])=O>>[NH2:1][C:2]1[CH:7]=[C:6]([Cl:17])[N:5]=[C:4]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[N:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178470783HCID 178470783, compound

Product 1

HCID 13060218HCID 13060218, compound

Procedure

A mixture of ethyl 2-(4-amino-6-hydroxypyrimidin-2-yl)acetate (15.8 g.) and phosphoryl chloride (75 ml.) was stirred for 4 hours under heating at 80° to 90° C. The resultant solution was allowed to cool and phosphoryl chloride was distilled off. The remaining oily substance was poured into a mixture of ice-water (200 ml.) and ethyl acetate (200 ml.). The resultant mixture was neutralized with an aqueous solution of ammonia and extracted with ethyl acetate. The extract was washed with water, dried over magnesium sulfate and then the solvent was distilled off. The resultant residue was washed with diisopropyl ether and then dried to give pale brown crystals of ethyl 2-(4-amino-6-chloropyrimidin-2-yl)acetate (8.1 g.), mp. 127° to 128° C.

Workup

  1. temperatureunder heating at 80° to 90° C
  2. temperatureto cool
  3. distillationphosphoryl chloride was distilled off
  4. additionThe remaining oily substance was poured into a mixture of ice-water (200 ml.) and ethyl acetate (200 ml.)
  5. extractionextracted with ethyl acetate
  6. washThe extract was washed with water
  7. dry with materialdried over magnesium sulfate
  8. distillationthe solvent was distilled off
  9. washThe resultant residue was washed with diisopropyl ether
  10. customdried

Sources & evidence

ORD record
ord-b40140602bb24559bdb80edb4756c10d
Source dataset
uspto-grants-1983_07
Patent number
US04395411

Reaction notes

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