Phosphorus oxychloride → 4-Chloro-6-fluoropyrido[3,2-D]pyrimidine

HRID 2256102Notes

Reaction equation

HRID 2256102 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]=[CH:7][NH:8][C:9](=O)[C:10]=2[N:11]=1.O=P(Cl)(Cl)[Cl:15]>>[Cl:15][C:9]1[C:10]2[N:11]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=2[N:6]=[CH:7][N:8]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 135427088HCID 135427088, compound

Product 1

HCID 106313224-Chloro-6-fluoropyrido[3,2-D]pyrimidineYield 100%

Procedure

A suspension of 6-fluoro-3H-pyrido[3,2-d]pyrimid-4-one (0.20 g, 1.21 mmol) in POCl3 (30 mL) is heated under reflux with stirring until homogeneous (2 h), and then for a further 1 h. Excess POCl3 is removed under reduced pressure, and the residue is partitioned between CH2Cl2 and saturated aqueous NaHCO3. Workup of the organic portion gives crude 4-chloro-6-fluoropyrido[3,2-d]pyrimidine (100%) as an unstable white solid which is used directly in the next step.

Workup

  1. temperatureis heated
  2. temperatureunder reflux
  3. waitfor a further 1 h
  4. customExcess POCl3 is removed under reduced pressure
  5. customthe residue is partitioned between CH2Cl2 and saturated aqueous NaHCO3

Sources & evidence

ORD record
ord-db8d1724fd48442ab56bef686c45e5cf
Source dataset
uspto-grants-1997_08
Patent number
US05654307

Reaction notes

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