Ethanol → 2-(5-phenylpentyl)pyrido[2,3-d]pyrimidin-4(3H)-one

HRID 2100462Notes

Reaction equation

HRID 2100462 reaction equation
[C:1]([C:3]1[C:4]([NH:9][C:10](=O)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[N:5][CH:6]=[CH:7][CH:8]=1)#[N:2].C([OH:25])C.OO.O>[OH-].[Na+]>[C:16]1([CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][C:10]2[NH:2][C:1](=[O:25])[C:3]3[CH:8]=[CH:7][CH:6]=[N:5][C:4]=3[N:9]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 784Hydrogen PeroxideHCID 962WaterHCID 866165906-Phenyl-hexanoic acid (3-cyano-pyridin-2-yl)-amide

Product 1

HCID 1358992442-(5-phenylpentyl)pyrido[2,3-d]pyrimidin-4(3H)-one

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

To 6-phenyl-hexanoic acid (3-cyano-pyridin-2-yl)-amide (360 mg, 1.2 mmol) in sodium hydroxide (6 ml, 5M) was added ethanol (0.1 ml) and hydrogen peroxide (3% in H2O, 1.5 ml). The reaction mixture was heated to reflux for 3 hours. Water was added, the solution was acidified (pH 5) and extracted with EtOAc (3 times). The combined organic phases were washed with brine, dried over Na2SO4, filtrated and concentrated in vacuo. Column chromatography on silica gel with CH2Cl2:MeOH 9:1 as eluent, followed by trituration from diethyl ether yielded 2-(5-phenyl-pentyl)-3H-pyrido[2,3-d]pyrimidin-4-one as a white solid, MS (m/e): 294.3 [M+H+].

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 3 hours
  3. extractionextracted with EtOAc (3 times)
  4. washThe combined organic phases were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltrated
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-66eee74215a04f16af4abad4395c7042
Source dataset
uspto-grants-2009_08
Patent number
US07572801B2

Reaction notes

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