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Diisopropylethylamine → 2-[2-[1-(6-Methyl-pyrimidin-4-yl)-piperidin-4-ylamino]-6-(4-trifluoromethyl-phenyl)-pyrimidin-4-yl]-propan-2-ol

HRID 451414
Notes
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Reaction equation

HRID 451414 reaction equation
Cl.Cl.[CH3:3][C:4]1[N:9]=[CH:8][N:7]=[C:6]([N:10]2[CH2:15][CH2:14][CH:13]([NH2:16])[CH2:12][CH2:11]2)[CH:5]=1.Cl[C:18]1[N:23]=[C:22]([C:24]([OH:27])([CH3:26])[CH3:25])[CH:21]=[C:20]([C:28]2[CH:33]=[CH:32][C:31]([C:34]([F:37])([F:36])[F:35])=[CH:30][CH:29]=2)[N:19]=1.C(N(CC)C(C)C)(C)C>CN1CCCC1=O.O>[CH3:3][C:4]1[N:9]=[CH:8][N:7]=[C:6]([N:10]2[CH2:15][CH2:14][CH:13]([NH:16][C:18]3[N:23]=[C:22]([C:24]([OH:27])([CH3:26])[CH3:25])[CH:21]=[C:20]([C:28]4[CH:33]=[CH:32][C:31]([C:34]([F:37])([F:35])[F:36])=[CH:30][CH:29]=4)[N:19]=3)[CH2:12][CH2:11]2)[CH:5]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 673421331-(6-Methylpyrimidin-4-yl)piperidin-4-amine dihydrochlorideHCID 866336402-[2-Chloro-6-(4-trifluoromethyl-phenyl)pyrimidine-4-yl]-propan-2-ol

Product 1

HCID 533533382-[2-[1-(6-Methyl-pyrimidin-4-yl)-piperidin-4-ylamino]-6-(4-trifluoromethyl-phenyl)-pyrimidin-4-yl]-propan-2-ol

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of 1-(6-methyl-pyrimidin-4-yl)-piperidin-4-ylamine dihydrochloride (53 mg, 0.2 mmol), 2-[2-chloro-6-(4-trifluoromethyl-phenyl)-pyrimidin-4-yl]-propan-2-ol (69.7 mg, 0.22 mmol)) and N,N-diisopropylethyl amine (120 L, 0.7 mmol) in N-methyl-pyrrolidinone (1 mL) was heated at 160° C. in a microwave oven for 5 hours. The reaction was diluted with water and extracted twice with ethyl acetate. The combined organic layers were washed with water, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using a gradient from AcOEt to AcOEt/EtOH 9:1 (v/v) as eluent. The title compound was obtained as a white solid (36 mg, 38%).

Workup

  1. extractionextracted twice with ethyl acetate
  2. washThe combined organic layers were washed with water
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel using a gradient from AcOEt to AcOEt/EtOH 9:1 (v/v) as eluent

Sources & evidence

ORD record
ord-0e8f10d7191f4045bcefb8b8c41d738a
Source dataset
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08486967B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes