Hydrochloric Acid → 4-[3-(4-Bromo-1-methyl-1H-pyrazol-3-yl)anilino]-2-(3-pyridinyl)-6-(trifluoromethyl)pyrimidine

HRID 2084112Notes

Reaction equation

HRID 2084112 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.[Br:18][C:19]1[C:20]([C:25]2[CH:26]=[C:27]([CH:29]=[CH:30][CH:31]=2)[NH2:28])=[N:21][N:22]([CH3:24])[CH:23]=1.Cl>O.C(O)C>[Br:18][C:19]1[C:20]([C:25]2[CH:26]=[C:27]([CH:29]=[CH:30][CH:31]=2)[NH:28][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)=[N:21][N:22]([CH3:24])[CH:23]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14859904-Chloro-2-(pyridin-3-yl)-6-(trifluoromethyl)pyrimidineHCID 27353913-(4-Bromo-1-Methyl-1H-Pyrazol-3-Yl)Aniline

Product 1

HCID 227324534-[3-(4-Bromo-1-methyl-1H-pyrazol-3-yl)anilino]-2-(3-pyridinyl)-6-(trifluoromethyl)pyrimidineYield 64.3%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

A mixture of 4-chloro-2-(3-pyridinyl)-6-(trifluoromethyl)pyrimidine (50 mg, 0.193 mmol), 3-(4-bromo-1-methyl-1H-pyrazol-3-yl)aniline (97 mg, 0.386 mmol) and aqueous 2N HCl (150 μl) in water:ethanol (1:1, 10 ml) was refluxed for 24 h. The mixture was cooled to room temperature, extracted with ethyl acetate (50 ml) and washed with water (1×25 ml). The ethyl acetate solution was acidified with aqueous 2N HCl (1×25 ml). The resulting precipitate was collected by filtration, washed with water and isolated as a pale white solid (59 mg, 64%). 1H NMR (DMSO-d6): 10.54 (s, 1H), 9.44 (d, J=2.1 Hz, 1H), 8.75 (dd, J=1.8, 4.8 Hz, 1H), 8.62-8.58 (m, 1H), 7.94 (s, 1H), 7.92 (s, 1H), 7.71 (s, 1H), 7.65 (t, J=8.3 Hz, 1H), 7.59-7.54 (m, 1H), 7.28 (d, J=8.1 Hz, 1H), 7.19 (s, 1H), 3.81 (s, 3H).

Workup

  1. temperaturewas refluxed for 24 h
  2. extractionextracted with ethyl acetate (50 ml)
  3. washwashed with water (1×25 ml)
  4. filtrationThe resulting precipitate was collected by filtration
  5. washwashed with water

Sources & evidence

ORD record
ord-a7a6e2b089f54cd182a66336e02058ac
Source dataset
uspto-grants-2004_04
Patent number
US06716851B2

Reaction notes

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