Trifluoroacetic acid → 5-(4-(1H-pyrazol-4-yl)pyrimidin-2-yloxy)-2-fluoro-4-methylbenzenamine

HRID 2060717Notes

Reaction equation

HRID 2060717 reaction equation
COC1C=CC(C[N:8]2[CH:12]=[C:11]([C:13]3[CH:18]=[CH:17][N:16]=[C:15]([O:19][C:20]4[C:21]([CH3:28])=[CH:22][C:23]([F:27])=[C:24]([NH2:26])[CH:25]=4)[N:14]=3)[CH:10]=[N:9]2)=CC=1.C(O)(C(F)(F)F)=O>ClCCl>[NH:8]1[CH:12]=[C:11]([C:13]2[CH:18]=[CH:17][N:16]=[C:15]([O:19][C:20]3[C:21]([CH3:28])=[CH:22][C:23]([F:27])=[C:24]([NH2:26])[CH:25]=3)[N:14]=2)[CH:10]=[N:9]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 673975355-(4-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)pyrimidin-2-yloxy)-2-fluoro-4-methylbenzenamine

Product 1

HCID 673990705-(4-(1H-pyrazol-4-yl)pyrimidin-2-yloxy)-2-fluoro-4-methylbenzenamineYield 70.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 5-(4-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)pyrimidin-2-yloxy)-2-fluoro-4-methylbenzenamine (0.5 g, 1.2 mmol) in dichloromethane (20 mL) was treated with TFA (5 mL) at 0° C. The mixture was then stirred at RT for 12 h. The solvent was removed in vacuo, the residue was washed with ether and treated with saturated ammonia solution. The solid was collected via filtration and dried under vacuum to give 5-(4-(1H-pyrazol-4-yl)pyrimidin-2-yloxy)-2-fluoro-4-methylbenzenamine (240 mg, 68%, yield). 1H NMR (400 MHz, MeOD): δ 8.41 (d, J=5.2 Hz, 1H), 8.21 (br s, 2H), 7.40 (d, J=5.2, 1H), 6.90 (d, J=11.6 Hz, 1H), 6.62 (d, J=8.0 Hz, 1H), 1.99 (s, 3H). MS (ESI) m/z: 286.1 (M+H+).

Workup

  1. customThe solvent was removed in vacuo
  2. washthe residue was washed with ether
  3. additiontreated with saturated ammonia solution
  4. filtrationThe solid was collected via filtration
  5. customdried under vacuum

Sources & evidence

ORD record
ord-98ca5e8c50c74ec1b8c97bf3a47f918b
Source dataset
uspto-grants-2012_10
Patent number
US08278331B2

Reaction notes

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