Trifluoroacetic acid → 2-(5-cyclopropyl-4-methyl-1H-pyrazol-3-yl)-5-methoxy-N-(pyridin-4-yl)pyrimidin-4-amine

HRID 1774527Notes

Reaction equation

[CH:1]1([C:4]2[N:8](CC3C=CC(OC)=CC=3)[N:7]=[C:6]([C:18]3[N:23]=[C:22]([NH:24][C:25]4[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=4)[C:21]([O:31][CH3:32])=[CH:20][N:19]=3)[C:5]=2[CH3:33])[CH2:3][CH2:2]1.FC(F)(F)C(O)=O.FC(F)(F)S(O)(=O)=O.[OH-].[Na+]>ClCCCl>[CH:1]1([C:4]2[NH:8][N:7]=[C:6]([C:18]3[N:23]=[C:22]([NH:24][C:25]4[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=4)[C:21]([O:31][CH3:32])=[CH:20][N:19]=3)[C:5]=2[CH3:33])[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 75 °C

Procedure

880 mg of 2-[5-cyclopropyl-1-(4-methoxybenzyl)-4-methyl-1H-pyrazol-3-yl]-5-methoxy-N-(pyridin-4-yl)pyrimidin-4-amine (2.0 mmol, 1.00 eq.) were dissolved in 7.8 mL of dry 1,2-dichloroethane. 4.6 mL trifluoroacetic acid (60 mmol, 30 eq.) and 1.8 mL trifluoromethanesulfonic acid (20 mmol, 10 eq.) were added at rt. The reaction mixture was stirred at 75° C. for 2 h. At 0° C. 2M sodiumhydroxide solution was added slowly. The solid was filtered off, dried in vacuo at 50° C. to provide 637 mg (1.96 mmol, 98%) of the analytically pure target compound.

Workup

customAt 0° C
filtrationThe solid was filtered off
customdried in vacuo at 50° C.
customto provide 637 mg (1.96 mmol, 98%) of the analytically pure target compound

Sources & evidence

ORD record: ord-0d4e86f36a7447f3baabd7d373e3d5aa
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09260412B2

Reaction notes

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