Triethylamine → HCID 53628954, compound

HRID 1784713Notes

Reaction equation

HRID 1784713 reaction equation
Cl.Cl.[CH:3]1([NH:9][C:10]2[CH:15]=[CH:14][C:13]([CH:16]3[CH2:21][CH2:20][CH2:19][NH:18][CH2:17]3)=[CH:12][CH:11]=2)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.C(N(CC)CC)C.Cl[C:30]1[N:35]([CH3:36])[C:34](=[O:37])[CH:33]=[C:32]([C:38]2[CH:43]=[CH:42][N:41]=[CH:40][CH:39]=2)[N:31]=1>O1CCCC1>[CH:3]1([NH:9][C:10]2[CH:15]=[CH:14][C:13]([CH:16]3[CH2:21][CH2:20][CH2:19][N:18]([C:30]4[N:35]([CH3:36])[C:34](=[O:37])[CH:33]=[C:32]([C:38]5[CH:39]=[CH:40][N:41]=[CH:42][CH:43]=5)[N:31]=4)[CH2:17]3)=[CH:12][CH:11]=2)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 112760814(3H)-Pyrimidinone, 2-chloro-3-methyl-6-(4-pyridinyl)-HCID 67117419HCID 67117419, compound

Product 1

HCID 53628954HCID 53628954, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(4-cyclohexylaminophenyl)-piperidine dihydrochloride salt (1.0 g, 3.02 mmol) and triethylamine (1.5 g, 14.8 mmol) in tetrahydrofuran (20 mL) was added 2-chloro-3-methyl-6-(pyridin-4-yl)-3H-pyrimidin-4-one (0.64 g, 2.89 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 2-(3-(4-cyclohexylaminophenyl)-piperidin-1-yl)-3-methyl-6-(pyridin-4-yl)-3H-pyrimidin-4-one (1.23 g, 2.77 mmol, 96%) 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-688e675da1f149ee9f2c802eb3e0d146
Source dataset
uspto-grants-2009_03
Patent number
US07504411B2

Reaction notes

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