4-Chloro-2-(pyridin-3-yl)-6-(trifluoromethyl)pyrimidine → HCID 22732404, compound

HRID 2084113Notes

Reaction equation

HRID 2084113 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[N:5]=[C:4]([C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)[N:3]=1.[NH2:18][C:19]1[CH:20]=[C:21]([C:25]2[CH:30]=[CH:29][N:28]=[C:27]([CH3:31])[N:26]=2)[CH:22]=[CH:23][CH:24]=1>>[CH3:31][C:27]1[N:26]=[C:25]([C:21]2[CH:20]=[C:19]([CH:24]=[CH:23][CH:22]=2)[NH:18][C:2]2[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[N:5]=[C:4]([C:12]3[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=3)[N:3]=2)[CH:30]=[CH:29][N:28]=1

Participants

3

Reactant 2

HCID 14859904-Chloro-2-(pyridin-3-yl)-6-(trifluoromethyl)pyrimidineHCID 27353973-(2-methylpyrimidin-4-yl)aniline

Product 1

HCID 22732404HCID 22732404, compound

Procedure

The title compound was prepared from a mixture of 4-chloro-2-(3-pyridinyl)-6-(trifluoromethyl)pyrimidine (50 mg, 0.193 mmol) and 4-(3-aminophenyl)-2-methylpyrimidine (71 mg, 0.386 mmol) similar to Example 58. The mixture was extracted with ethyl acetate (50 ml), washed with water (1×25 ml) and with aqueous 2N HCl (1×25 ml). The acidic aqueous solution was basified with aqueous 2N NaOH to pH 10-12. The resulting precipitate was filtered, washed with water and isolated as a light tan solid (18 mg, 23%). 1H NMR (CDCl3): 9.71 (d, J=2.4 Hz, 1H), 8.77-8.72 (m, 3H), 8.38 (s, 1H), 7.89 (d, J=7.2 Hz, 1H), 7.69-7.54 (m, 4H), 7.45-7.41 (m, 1H), 6.95 (s, 1H), 2.83 (s, 3H).

Workup

  1. extractionThe mixture was extracted with ethyl acetate (50 ml)
  2. washwashed with water (1×25 ml) and with aqueous 2N HCl (1×25 ml)
  3. filtrationThe resulting precipitate was filtered
  4. washwashed with water

Sources & evidence

ORD record
ord-8bf7f8700e4b46038824bd0dba120129
Source dataset
uspto-grants-2004_04
Patent number
US06716851B2

Reaction notes

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