Phosphorus oxychloride → HCID 86715503, compound

HRID 2284592Notes

Reaction equation

HRID 2284592 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([C:14]3[NH:19][C:18](=O)[N:17]=[CH:16][CH:15]=3)=[CH:12][CH:11]=[CH:10][N:9]=2)=[CH:4][C:3]=1[CH3:21].O=P(Cl)(Cl)[Cl:24]>>[Cl:24][C:18]1[N:19]=[C:14]([C:13]2[C:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[C:3]([CH3:21])[CH:4]=3)=[N:9][CH:10]=[CH:11][CH:12]=2)[CH:15]=[CH:16][N:17]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 86715501HCID 86715501, compound

Product 1

HCID 86715503HCID 86715503, compound

Procedure

6-(2-(4-Fluoro-3-methylphenyl)pyridin-3-yl)pyrimidin-2(1H)-one (0.83 g) and POCl3 (3 mL) were heated at 130° C. under nitrogen. The reaction mixture was cooled to room temperature upon completion of the reaction (2 h). The volatiles were removed and quenched the concentrate with ice. The semi-heterogeneous slurry was neutralized with aq. NaHCO3 solution while stirring, warmed to room temperature and diluted with EtOAc (200 mL). The organic layer was separated, stirred over MgSO4, filtered, concentrated and purified by flash chromatography (Combiflash® companion System® with RediSep® silica gel column 12 g and 10-50% EtOAc/Hexanes as eluting solvent) to obtain 2-chloro-4-(2-(4-fluoro-3-methylphenyl)pyridin-3-yl)pyrimidine as a clear viscous liquid.

Workup

  1. customThe volatiles were removed
  2. customquenched the
  3. concentrationconcentrate with ice
  4. temperaturewarmed to room temperature
  5. additiondiluted with EtOAc (200 mL)
  6. customThe organic layer was separated
  7. stirringstirred over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. custompurified by flash chromatography (Combiflash® companion System® with RediSep® silica gel column 12 g and 10-50% EtOAc/Hexanes as eluting solvent)

Sources & evidence

ORD record
ord-6d3817ca90064b6fb3d63d4ed81f57a2
Source dataset
uspto-grants-2015_09
Patent number
US09145433B2

Reaction notes

Loading…