N,N-Dimethylaniline → HCID 22169999, compound

HRID 1822778Notes

Reaction equation

HRID 1822778 reaction equation
CN(C)C1C=CC=CC=1.[CH2:10]([C:14]1[N:19]=[C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=2)[NH:17][C:16](=O)[CH:15]=1)[CH2:11][CH2:12][CH3:13].P(Cl)(Cl)([Cl:30])=O>>[CH2:10]([C:14]1[CH:15]=[C:16]([Cl:30])[N:17]=[C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=2)[N:19]=1)[CH2:11][CH2:12][CH3:13]

Participants

4

Reactant 3

HCID 949N,N-DimethylanilineHCID 24813Phosphorus oxychlorideHCID 135788278HCID 135788278, compound

Product 1

HCID 22169999HCID 22169999, compound

Procedure

A solution of N, N-dimethylaniline (0.31 mL) and 6-butyl-2-(3-fluoro-phenyl)-3H-pyrimidin-4-one (0.3 g) in 6 mL phosphorus oxychloride was heated in a sealed tube for 2.5 h at 125° C. The solution was allowed to cool and the phosphorous oxychloride were removed in vacuo. The remaining residue was washed four times with diethyl ether and the combined ether portions were washed with 0.5 M hydrochloric acid, dried over magnesium sulfate, and concentrated in vacuo to yield 4-butyl-6-chloro-2-(3-fluoro-phenyl)-pyrimidine (0.20 g).

Workup

  1. temperatureto cool
  2. customthe phosphorous oxychloride were removed in vacuo
  3. washThe remaining residue was washed four times with diethyl ether
  4. washthe combined ether portions were washed with 0.5 M hydrochloric acid
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8312d542c2b444bf8a63bd340f10c70d
Source dataset
uspto-grants-2006_05
Patent number
US07037916B2

Reaction notes

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