Phosphorus oxychloride → 4-Chloro-6-phenylpyrimidine

HRID 1166154

Reaction equation

HRID 1166154 reaction equation
O[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:5]=[CH:4][N:3]=1.P(Cl)(Cl)([Cl:16])=O>>[Cl:16][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:5]=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178515560HCID 178515560, compound

Product 1

HCID 5934294-Chloro-6-phenylpyrimidineYield 93.5%

Procedure

Crude 4-hydroxy-6-phenylpyrimidine (3.65 g) was heated to reflux with phosphoryl chloride (40 ml) for 90 minutes. The reaction mixture was cooled and then concentrated under reduced pressure to afford a brown solid. The brown solid was partitioned between water and ether and the combined ether extracts washed with brine, dried and evaporated to give 4-chloro-6-phenylpyrimidine (2.18 g, 93.5% pure by GC analysis) as a yellow solid which was used directly in the next stage.

Workup

  1. temperatureThe reaction mixture was cooled
  2. concentrationconcentrated under reduced pressure
  3. customto afford a brown solid
  4. customThe brown solid was partitioned between water and ether
  5. washthe combined ether extracts washed with brine
  6. customdried
  7. customevaporated

Sources & evidence

ORD record
ord-5c9af44dc84d48af91e26c2dbc3c421d
Source dataset
uspto-grants-2003_09
Patent number
US06613773B2

Linked notes

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