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Triethylamine → HCID 57593892, compound

HRID 1784710
Notes
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Reaction equation

HRID 1784710 reaction equation
Cl.Cl.Cl.[CH3:4][N:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:16]=[CH:15][C:14]([CH:17]3[CH2:22][CH2:21][CH2:20][NH:19][CH2:18]3)=[CH:13][CH:12]=2)[CH2:7][CH2:6]1.C(N(CC)CC)C.Cl[C:31]1[N:36]([CH3:37])[C:35](=[O:38])[CH:34]=[C:33]([C:39]2[CH:44]=[CH:43][N:42]=[CH:41][CH:40]=2)[N:32]=1>O1CCCC1>[CH3:37][N:36]1[C:35](=[O:38])[CH:34]=[C:33]([C:39]2[CH:44]=[CH:43][N:42]=[CH:41][CH:40]=2)[N:32]=[C:31]1[N:19]1[CH2:20][CH2:21][CH2:22][CH:17]([C:14]2[CH:13]=[CH:12][C:11]([N:8]3[CH2:9][CH2:10][N:5]([CH3:4])[CH2:6][CH2:7]3)=[CH:16][CH:15]=2)[CH2:18]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 112760814(3H)-Pyrimidinone, 2-chloro-3-methyl-6-(4-pyridinyl)-HCID 67117384HCID 67117384, compound

Product 1

HCID 57593892HCID 57593892, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(4-(4-methylpiperazin-1-yl)-phenyl)-piperidine trihydrochloride salt (0.4 g, 1.08 mmol) and triethylamine (0.6 g, 5.93 mmol) in tetrahydrofuran (10 mL) was added 2-chloro-3-methyl-6-(pyridin-4-yl)-3H-pyrimidin-4-one (0.22 g, 0.99 mmol) portionwise. After stirring for 12 h, the resulting suspension was partitioned between chloroform and 1N sodium hydroxide. The aqueous layer was extracted with chloroform. The combined organic layer was washed with brine, dried over magnesium sulfate, and concentrated in vacuo. The residue was purified by silica gel chromatography eluting 5-10% methanol in chloroform to furnish 3-methyl-2-(3-(4-(4-methylpiperazin-1-yl)-phenyl)-piperidin-1-yl)-6-(piridin-4-yl)-3H-pyrimidin-4-one (0.31 g, 0.70 mmol; 71%) as white crystals.

Workup

  1. customthe resulting suspension was partitioned between chloroform and 1N sodium hydroxide
  2. extractionThe aqueous layer was extracted with chloroform
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel chromatography
  7. washeluting 5-10% methanol in chloroform

Sources & evidence

ORD record
ord-5756c3fc9e6b4483bf935bfc4dd79987
Source dataset
uspto-grants-2009_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07504411B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes