Dimethylformamide → 2-Chloro-4-(pyridin-4-yl)pyrimidine

HRID 398036Notes

Reaction equation

HRID 398036 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[CH:12]=[CH:11][NH:10][C:9](=O)[N:8]=2)=[CH:3][CH:2]=1.S(Cl)([Cl:16])=O.CN(C)C=O>>[Cl:16][C:9]1[N:8]=[C:7]([C:4]2[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=2)[CH:12]=[CH:11][N:10]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 178517538HCID 178517538, compound

Product 1

HCID 230004542-Chloro-4-(pyridin-4-yl)pyrimidine

Procedure

With ice-bath cooling under argon, 4-(4-pyridyl)-2(1H)-pyrimidinone (13.45 g, 77.7 mmol) and thionyl chloride (92 ml) were combined. N,N-Dimethylformamide (13.2 ml, 170.5 mmol) was added slowly and the mixture was heated to reflux for 1 h. It was evaporated and co-distilled with toluene. At 0° C., water was added to the remainder, then 10% ammonium hydroxide until neutral followed by extraction with dichloromethane. Drying of the organic solution was followed by evaporation and the resultant solid was recrystallized from acetone. MS (m/z): 192.1,194.0 (M+H)+; C9H6ClN3 requir. 191.6.

Workup

  1. temperatureWith ice-bath cooling under argon
  2. temperaturethe mixture was heated
  3. temperatureto reflux for 1 h
  4. customIt was evaporated
  5. additionAt 0° C., water was added to the remainder
  6. extraction10% ammonium hydroxide until neutral followed by extraction with dichloromethane
  7. customDrying of the organic solution
  8. customwas followed by evaporation
  9. customthe resultant solid was recrystallized from acetone

Sources & evidence

ORD record
ord-97f998a221754a3eb84459a17740ee52
Source dataset
uspto-grants-2003_08
Patent number
US06610698B2

Reaction notes

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