N,N-Diethylaniline → 5-Chloro-6-(2-chloro-6-fluorophenyl)-7-methylimidazo[1,2-a]pyrimidine

HRID 1348550Notes

Reaction equation

HRID 1348550 reaction equation
O[C:2]1[N:7]2[CH:8]=[CH:9][N:10]=[C:6]2[N:5]=[C:4]([CH3:11])[C:3]=1[C:12]1[C:17]([F:18])=[CH:16][CH:15]=[CH:14][C:13]=1[Cl:19].C(N(CC)C1C=CC=CC=1)C.P(Cl)(Cl)([Cl:33])=O>>[Cl:33][C:2]1[N:7]2[CH:8]=[CH:9][N:10]=[C:6]2[N:5]=[C:4]([CH3:11])[C:3]=1[C:12]1[C:17]([F:18])=[CH:16][CH:15]=[CH:14][C:13]=1[Cl:19]

Participants

4

Reactant 3

HCID 7061N,N-DiethylanilineHCID 24813Phosphorus oxychlorideHCID 178432390HCID 178432390, compound

Product 1

HCID 230183375-Chloro-6-(2-chloro-6-fluorophenyl)-7-methylimidazo[1,2-a]pyrimidine

Procedure

A mixture of 0.16 g of 5-hydroxy-6-(2-chloro-6-fluorophenyl)-7-methylimidazo[1,2-a]pyrimidine, 0.20 g of N,N-diethylaniline and 2 ml of phosphorus oxychloride was refluxed under heating for 26 hours. The reaction mixture was concentrated, and dichloromethane and aqueous saturated sodium bicarbonate solution were added to the residue. The separated organic layer was washed with water, dried over sodium sulfate and concentrated. The residue was subjected to silica gel chromatography to give 45mg of 5-chloro-6-(2-chloro-6-fluorophenyl)-7-methylimidazo[1,2-a]pyrimidine.

Workup

  1. temperaturewas refluxed
  2. temperatureunder heating for 26 hours
  3. concentrationThe reaction mixture was concentrated
  4. additiondichloromethane and aqueous saturated sodium bicarbonate solution were added to the residue
  5. washThe separated organic layer was washed with water
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-23fce526404044e9a47c6e0dc7f178da
Source dataset
uspto-grants-2007_05
Patent number
US07211545B2

Reaction notes

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