Phosphorus oxychloride → 2-Chloro-3-methyl-6-pyridin-4-yl-5-m-tolyl-3H-pyrimidin-4-one

HRID 480438Notes

Reaction equation

HRID 480438 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[CH:10]=2)=[C:5]([C:16]2[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=2)[NH:4][C:3]1=O.P(Cl)(Cl)([Cl:25])=O>>[Cl:25][C:3]1[N:2]([CH3:1])[C:7](=[O:8])[C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[CH:10]=2)=[C:5]([C:16]2[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=2)[N:4]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 223465713-methyl-5-(3-methylphenyl)-6-(4-pyridyl)-2,4(1H,3H)-pyrimidindione

Product 1

HCID 161156882-Chloro-3-methyl-6-pyridin-4-yl-5-m-tolyl-3H-pyrimidin-4-one

Procedure

A mixture of 3-methyl-5-(3-methylphenyl)-6-(4-pyridyl)-2,4(1H,3H) -pyrimidindione (12.5 g, 0.043 mol) and phosphorus oxychloride (65 ml) was refluxed for 16 h. The excess of phosphorus oxychloride was evaporated followed by co-distillation with toluene. The remainder was carefully partitioned between dichloromethane and aqueous sodium hydrogencarbonate. The organic solution was washed with water, dried and evaporated to leave the title compound. MS (m/z): 312 (M)+; C17H14ClN3O requir. 311.8.

Workup

  1. temperaturewas refluxed for 16 h
  2. customThe excess of phosphorus oxychloride was evaporated
  3. customThe remainder was carefully partitioned between dichloromethane and aqueous sodium hydrogencarbonate
  4. washThe organic solution was washed with water
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-1620e43820904b99935bc8ec6e489a63
Source dataset
uspto-grants-2003_11
Patent number
US06649604B2

Reaction notes

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