2-chloro-N-(5-methyl-1H-pyrazol-3-yl)-5-(trifluoromethyl)pyrimidin-4-amine → N2-(2,5-dimethyl-4-(piperidin-4-yl)phenyl)-N4-(5-methyl-1H-pyrazol-3-yl)-5-(trifluoromethyl)pyrimidine-2,4-diamine

HRID 536404Notes

Reaction equation

HRID 536404 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:13]=[C:12]([CH3:14])[NH:11][N:10]=2)[C:5]([C:15]([F:18])([F:17])[F:16])=[CH:4][N:3]=1.C(OC([N:26]1[CH2:31][CH2:30][CH:29]([C:32]2[CH:37]=[C:36]([CH3:38])[C:35]([NH2:39])=[CH:34][C:33]=2[CH3:40])[CH2:28][CH2:27]1)=O)(C)(C)C>Cl.CC(O)C>[CH3:38][C:36]1[CH:37]=[C:32]([CH:29]2[CH2:28][CH2:27][NH:26][CH2:31][CH2:30]2)[C:33]([CH3:40])=[CH:34][C:35]=1[NH:39][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:13]=[C:12]([CH3:14])[NH:11][N:10]=2)[C:5]([C:15]([F:18])([F:17])[F:16])=[CH:4][N:3]=1

Participants

5

Reactant 2

HCID 582551692-chloro-N-(5-methyl-1H-pyrazol-3-yl)-5-(trifluoromethyl)pyrimidin-4-amineHCID 67155205Tert-butyl-4-(4-amino-2,5-dimethylphenyl)piperidine-1-carboxylate

Product 1

HCID 58254965N2-(2,5-dimethyl-4-(piperidin-4-yl)phenyl)-N4-(5-methyl-1H-pyrazol-3-yl)-5-(trifluoromethyl)pyrimidine-2,4-diamine

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 3776IsopropanolSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 2-chloro-N-(5-methyl-1H-pyrazol-3-yl)-5-(trifluoromethyl)pyrimidin-4-amine (513.0 mg, 0.9 mmol), tert-butyl-4-(4-amino-2,5-dimethylphenyl)piperidine-1-carboxylate (282.7 mg, 0.9 mmol), and concentrated aqueous HCl (10 drops) in i-PrOH (12 mL) was heated at 150° C. in a microwave reactor for 30 min. The crude product was purified by RP-HPLC to afford N2-(2,5-dimethyl-4-(piperidin-4-yl)phenyl)-N4-(5-methyl-1H-pyrazol-3-yl)-5-(trifluoromethyl)pyrimidine-2,4-diamine; ESMS m/z 446.2 (M+H+).

Workup

  1. customThe crude product was purified by RP-HPLC

Sources & evidence

ORD record
ord-373bb144ec124d60b00a35cd08c259f6
Source dataset
uspto-grants-2014_10
Patent number
US08859574B2

Reaction notes

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