Trifluoroacetic acid → 5-chloro-N4-(5-methyl-1H-pyrazol-3-yl)-N2-(4-methyl-5-(piperidin-4-yl)pyridin-2-yl)pyrimidine-2,4-diamine

HRID 2093819Notes

Reaction equation

HRID 2093819 reaction equation
[Cl:1][C:2]1[C:3]([NH:29][C:30]2[CH:34]=[C:33]([CH3:35])[N:32](C3CCCCO3)[N:31]=2)=[N:4][C:5]([NH:8][C:9]2[N:14]=[CH:13][C:12]([CH:15]3[CH2:20][CH2:19][N:18](C(OC(C)(C)C)=O)[CH2:17][CH2:16]3)=[C:11]([CH3:28])[CH:10]=2)=[N:6][CH:7]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:1][C:2]1[C:3]([NH:29][C:30]2[CH:34]=[C:33]([CH3:35])[NH:32][N:31]=2)=[N:4][C:5]([NH:8][C:9]2[CH:10]=[C:11]([CH3:28])[C:12]([CH:15]3[CH2:16][CH2:17][NH:18][CH2:19][CH2:20]3)=[CH:13][N:14]=2)=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67167118tert-butyl 4-(6-(5-chloro-4-(5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-3-ylamino)pyrimidin-2-ylamino)-4-methylpyridin-3-yl)piperidine-1-carboxylate

Product 1

HCID 671691565-chloro-N4-(5-methyl-1H-pyrazol-3-yl)-N2-(4-methyl-5-(piperidin-4-yl)pyridin-2-yl)pyrimidine-2,4-diamine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-(6-(5-chloro-4-(5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-3-ylamino)pyrimidin-2-ylamino)-4-methylpyridin-3-yl)piperidine-1-carboxylate in DCM (1 mL), was added TFA (1 mL). The mixture was stirred for 1 h and concentrated to afford 5-chloro-N4-(5-methyl-1H-pyrazol-3-yl)-N2-(4-methyl-5-(piperidin-4-yl)pyridin-2-yl)pyrimidine-2,4-diamine as brownish oil. The product was used directly for subsequent reactions without further purification.

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-95354e33f98b44eeb9651bda0ea346f8
Source dataset
uspto-grants-2013_05
Patent number
US08445505B2

Reaction notes

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