Triethylamine → HCID 53628958, compound

HRID 1784719Notes

Reaction equation

HRID 1784719 reaction equation
[N:1]1([C:6]2[CH:11]=[CH:10][C:9]([CH:12]3[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]3)=[CH:8][CH:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.Cl[C:26]1[N:31]([CH3:32])[C:30](=[O:33])[CH:29]=[C:28]([C:34]2[CH:39]=[CH:38][N:37]=[CH:36][CH:35]=2)[N:27]=1>O1CCCC1>[CH3:32][N:31]1[C:30](=[O:33])[CH:29]=[C:28]([C:34]2[CH:39]=[CH:38][N:37]=[CH:36][CH:35]=2)[N:27]=[C:26]1[N:15]1[CH2:16][CH2:17][CH:12]([C:9]2[CH:8]=[CH:7][C:6]([N:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)=[CH:11][CH:10]=2)[CH2:13][CH2:14]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 112760814(3H)-Pyrimidinone, 2-chloro-3-methyl-6-(4-pyridinyl)-HCID 67117406HCID 67117406, compound

Product 1

HCID 53628958HCID 53628958, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 4-(4-pyrrolidin-1-yl-phenyl)-piperidine (215 mg, 0.933 mmol) and triethylamine (391 mg, 3.86 mmol), 2-chloro-3-methyl-6-(pyridin-4-yl)-3H-pyrimidin-4-one (187 mg, 0.844 mmol) in tetrahydrofuran (10 mL) was refluxed for 5 hr. The resulting solution was diluted with tetrahydrofuran and filtrated. After removal of the solvents under reduced pressure and the purification of the resulting residue by CHEM ELUT CE1010 (manufactured by VARIAN) eluting dichloromethane/ethanol (15/1, v/v) and wash with ethyl acetate afforded 3-methyl-6-pyridin-4-yl-2-(4-(4-pyrrolidin-1-yl-phenyl)-piperidin-1-yl)-3H-pyrimidin-4-one (284 mg, 81%) as a solid.

Workup

  1. filtrationfiltrated
  2. customAfter removal of the solvents under reduced pressure
  3. customthe purification of the resulting residue by CHEM ELUT CE1010 (manufactured by VARIAN)
  4. washeluting dichloromethane/ethanol (15/1
  5. washv/v) and wash with ethyl acetate

Sources & evidence

ORD record
ord-12034e504d8748dcb585172770766ce8
Source dataset
uspto-grants-2009_03
Patent number
US07504411B2

Reaction notes

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