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Triethylamine → n4-(5-Methyl-1h-pyrazol-3-yl)-5-(trifluoromethyl)pyrimidine-2,4-diamine

HRID 1897723
Notes
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Reaction equation

HRID 1897723 reaction equation
FC1C=C(C2CCNCC2)C(C)=CC=1[NH:15][C:16]1[N:21]=[C:20]([NH:22][C:23]2[CH:27]=[C:26]([CH3:28])[NH:25][N:24]=2)[C:19]([C:29]([F:32])([F:31])[F:30])=[CH:18][N:17]=1.BrCC1CC1(F)F.C(N(CC)CC)C>CN(C=O)C>[CH3:28][C:26]1[NH:25][N:24]=[C:23]([NH:22][C:20]2[C:19]([C:29]([F:32])([F:31])[F:30])=[CH:18][N:17]=[C:16]([NH2:15])[N:21]=2)[CH:27]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27614022-(Bromomethyl)-1,1-difluorocyclopropaneHCID 44612737N2-(2-fluoro-5-methyl-4-(piperidin-4-yl)phenyl)-N4-(5-methyl-1H-pyrazol-3-yl)-5-(trifluoromethyl)pyrimidine-2,4-diamine

Product 1

HCID 86653272n4-(5-Methyl-1h-pyrazol-3-yl)-5-(trifluoromethyl)pyrimidine-2,4-diamine

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Conditions

Temperature
60 °C

Procedure

A mixture of N2-(2-fluoro-5-methyl-4-(piperidin-4-yl)phenyl)-N4-(5-methyl-1H-pyrazol-3-yl)-5-(trifluoromethyl)pyrimidine-2,4-diamine (100 mg, 0.22 mmol), 2-(bromomethyl)-1,1-difluorocyclopropane (76.4 mg, 0.45 mmol) and triethylamine (60.6 μL, 0.42 mmol) in 1 mL of DMF was heated at 60° C. in a microwave reactor for 2 h. The crude product was purified by RP-HPLC to afford N2-(4-(1-(2,2-difluorocyclopropyl)methyl)piperidin-4-yl)-2-fluoro-5-methylphenyl)-N4— (5-methyl-1H-pyrazol-3-yl)-5-(trifluoromethyl)pyrimidine-2,4-diamine; ESMS m/z 540.2 (M+H+).

Workup

  1. customThe crude product was purified by RP-HPLC

Sources & evidence

ORD record
ord-89fde482e4a54b9c918a3408a2e78fc7
Source dataset
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08519129B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes