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

HRID 1776393Notes

Reaction equation

HRID 1776393 reaction equation
[CH3:1][O:2][C:3]1[C:4]([NH:27][C:28]2[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=2)=[N:5][C:6]([C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11](CC3C=CC(OC)=CC=3)[N:10]=2)=[N:7][CH:8]=1.FC(F)(F)C(O)=O.FC(F)(F)S(O)(=O)=O.[OH-].[Na+]>ClCCCl>[NH:11]1[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:9]([C:6]2[N:5]=[C:4]([NH:27][C:28]3[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=3)[C:3]([O:2][CH3:1])=[CH:8][N:7]=2)=[N:10]1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 62406Trifluoromethanesulfonic acidHCID 867324175-methoxy-2-[1-(4-methoxybenzyl)-1H-indazol-3-yl]-N-(pyridin-4-yl)pyrimidin-4-amine

Product 1

HCID 867324182-(1H-indazol-3-yl)-5-methoxy-N-(pyridin-4-yl)pyrimidin-4-amine

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

13.4 g of 5-methoxy-2-[1-(4-methoxybenzyl)-1H-indazol-3-yl]-N-(pyridin-4-yl)-pyrimidin-4-amine (1-5-1, 30.6 mmol, 1 eq.) was suspended in 121 ml of 1,2-dichloroethan. First 71 ml of trifluoroacetic acid (918 mmol, 30 eq.) were added dropwise, followed by 27 ml of trifluoromethanesulfonic acid (306 mmol, 10 eq.). The reaction mixture was stirred for three days under nitrogen atmosphere. The mixture was cooled with an ice bath to +3° C., upon which 2M aq. sodium hydroxide solution was added until pH=12. The resulting brown suspension was stirred for 18 hours at room temperature and then the precipitate was filtered off and dried under vacuo at 70° C. to yield 9.74 g (27.7 mmol, 90.3%) of the analytically pure target compound as a light brown solid.

Workup

  1. additionwas added until pH=12
  2. stirringThe resulting brown suspension was stirred for 18 hours at room temperature
  3. filtrationthe precipitate was filtered off
  4. customdried under vacuo at 70° C.
  5. customto yield 9.74 g (27.7 mmol, 90.3%) of the analytically pure target compound as a light brown solid

Sources & evidence

ORD record
ord-08e2d78a4150420fb3be910688b0ef06
Source dataset
uspto-grants-2016_02
Patent number
US09265763B2

Reaction notes

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