Phosphorus oxychloride → HCID 21708399, compound

HRID 651420Notes

Reaction equation

HRID 651420 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:4]=[C:5]([CH:14]=[CH:15][CH:16]=1)[CH2:6][C:7]1[N:12]=[CH:11][NH:10][C:9](=O)[CH:8]=1.P(Cl)(Cl)([Cl:21])=O>>[F:1][C:2]([F:18])([F:17])[C:3]1[CH:4]=[C:5]([CH:14]=[CH:15][CH:16]=1)[CH2:6][C:7]1[N:12]=[CH:11][N:10]=[C:9]([Cl:21])[CH:8]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 135704063HCID 135704063, compound

Product 1

HCID 21708399HCID 21708399, compound

Procedure

Under nitrogen atmosphere, 6-(3-trifluoromethylbenzyl)pyrimidin-4-one (7.0 g, 0.027 mol) is dissolved in phosphorus oxychloride (30 ml) and is refluxed for 1.5 hours. After cooling the solution is concentrated under reduced pressure. The solid is then dissolved in ethyl acetate, washed with water, saturated brine, dried and the crude product purified by flash column chromatography to give 6-(3-trifluoromethylbenzyl)-4-chloro-pyrimidine (6.3 g).

Workup

  1. temperatureis refluxed for 1.5 hours
  2. temperatureAfter cooling the solution
  3. concentrationis concentrated under reduced pressure
  4. dissolutionThe solid is then dissolved in ethyl acetate
  5. washwashed with water, saturated brine
  6. customdried
  7. customthe crude product purified by flash column chromatography

Sources & evidence

ORD record
ord-cc81e100bf7445b0aae543e24c2ebbfe
Source dataset
uspto-grants-2001_08
Patent number
US06281219B1

Reaction notes

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