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Diisopropylethylamine → (4-Benzyl-6-methyl-pyrimidin-2-yl)-[1-(2-methyl-pyrimidin-4-yl)-piperidin-4-yl]-amine

HRID 451410
Notes
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Reaction equation

HRID 451410 reaction equation
Cl.Cl.[CH3:3][C:4]1[N:9]=[C:8]([N:10]2[CH2:15][CH2:14][CH:13]([NH2:16])[CH2:12][CH2:11]2)[CH:7]=[CH:6][N:5]=1.[CH2:17]([C:24]1[CH:29]=[C:28]([CH3:30])[N:27]=[C:26](Cl)[N:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(N(CC)C(C)C)(C)C>CN1CCCC1=O.O>[CH2:17]([C:24]1[CH:29]=[C:28]([CH3:30])[N:27]=[C:26]([NH:16][CH:13]2[CH2:14][CH2:15][N:10]([C:8]3[CH:7]=[CH:6][N:5]=[C:4]([CH3:3])[N:9]=3)[CH2:11][CH2:12]2)[N:25]=1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 673429791-(2-Methylpyrimidin-4-yl)piperidin-4-amine dihydrochlorideHCID 866336184-Benzyl-2-chloro-6-methyl-pyrimidine

Product 1

HCID 53353336(4-Benzyl-6-methyl-pyrimidin-2-yl)-[1-(2-methyl-pyrimidin-4-yl)-piperidin-4-yl]-amine

Reagents, catalysts & solvents 2

HCID 962WaterSolvent
HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of 1-(2-methyl-pyrimidin-4-yl)-piperidin-4-ylamine dihydrochloride (53 mg, 0.2 mmol), 4-benzyl-2-chloro-6-methylpyrimidin (48.1 mg, 0.22 mmol) and N,N-diisopropylethyl amine (120 L, 0.7 mmol) in N-methyl-pyrrolidinone (1 mL) was heated at 200° C. in a microwave oven for 1 hour. 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 with AcOEt/EtOH 9:1 (v/v) as eluent. The title compound was obtained as a light yellow solid (16 mg, 21%).

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 with AcOEt/EtOH 9:1 (v/v) as eluent

Sources & evidence

ORD record
ord-2cab62e0e16a4ee5a669efd938bde70e
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