2-Fluoroaniline → HCID 178505594, compound

HRID 489962Notes

Reaction equation

HRID 489962 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[C:9]([C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=3)=[N:10][NH:11][CH:12]=2)[CH:5]=[CH:4][N:3]=1.[F:20][C:21]1[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=1[NH2:23]>CO>[F:20][C:21]1[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=1[NH:23][C:2]1[N:7]=[C:6]([C:8]2[C:9]([C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=3)=[N:10][NH:11][CH:12]=2)[CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 95842-FluoroanilineHCID 178505591HCID 178505591, compound

Product 1

HCID 178505594HCID 178505594, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 887MethanolCatalyst

Conditions

Temperature
180 °C

Procedure

A mixture of 2-chloro-4-[3-(4-fluorophenyl)-1H-pyrazol-4-yl]pyrimidine (0.37 g; 0.0013 mol; prepared as set forth in Example A-299), 7 mL of 2-fluoroaniline and 2 drops of methanol was heated at 180° C. in a sealed tube for 16 hours. Excess amine was removed by vacuum distillation and the residue was treated with ethyl acetate to give 0.35 g of N-(2-fluorophenyl)-4-[3-(4-fluorophenyl)-1H-pyrazol-4-yl]-2-pyrimidinamine as a yellow solid (77%), mp: 239-240° C. Anal. Calc'd. for C1913F2N5: C, 65.33; H, 3.75; N, 20.05. Found: C, 64.95; H, 3.80; N, 19.77.

Workup

  1. customprepared
  2. customExcess amine was removed by vacuum distillation
  3. additionthe residue was treated with ethyl acetate

Sources & evidence

ORD record
ord-fd12365a232d42fc9ed22263b786b8e7
Source dataset
uspto-grants-2005_12
Patent number
US06979686B1

Reaction notes

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