Water → 2-(3-Benzoylpiperidin-1-yl)-3-methyl-6-pyridin-4-yl-3H-pyrimidin-4-one

HRID 32305Notes

Reaction equation

HRID 32305 reaction equation
Cl.[C:2]([CH:10]1[CH2:15][CH2:14][CH2:13][NH:12][CH2:11]1)(=[O:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl[C:17]1[N:22]([CH3:23])[C:21](=[O:24])[CH:20]=[C:19]([C:25]2[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=2)[N:18]=1.C(N(CC)CC)C.O>O1CCCC1>[C:2]([CH:10]1[CH2:15][CH2:14][CH2:13][N:12]([C:17]2[N:22]([CH3:23])[C:21](=[O:24])[CH:20]=[C:19]([C:25]3[CH:26]=[CH:27][N:28]=[CH:29][CH:30]=3)[N:18]=2)[CH2:11]1)(=[O:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 112760814(3H)-Pyrimidinone, 2-chloro-3-methyl-6-(4-pyridinyl)-HCID 197720583-Benzoylpiperidine hydrochloride

Product 1

HCID 101562632-(3-Benzoylpiperidin-1-yl)-3-methyl-6-pyridin-4-yl-3H-pyrimidin-4-oneYield 121.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-benzoylpiperidine hydrochloride (109 mg, 0.60 mmol), 2-chloro-3-methyl-6-(4-pyridyl)-pyrimidine-4-one (118 mg, 0.40 mmol) and triethylamine (0.50 ml, 4.00 mmol) in tetrahydrofuran (6 ml) was stirred at room temperature for several hours. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with brine, dried over Na2SO4 and evaporated in vacuo. Purification of the residue by silica gel column chromatography (ethyl acetate) gave the title compound (182 mg, 61%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. customevaporated in vacuo
  5. customPurification of the residue by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-6ff4723a1c0e4efeb7f4aa784eb88b84
Source dataset
uspto-grants-2008_09
Patent number
US07427615B2

Reaction notes

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