Acetic Acid → 4-(5-(6-(Hydroxymethyl)-3-methyl-2,4-dioxo-1-(3-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydropyrimidin-5-yl)-1H-pyrazol-1-yl)benzonitrile

HRID 576785Notes

Reaction equation

HRID 576785 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[C:6]([C:9]2[N:13]([C:14]3[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=3)[N:12]=[CH:11][CH:10]=2)=[C:5]([CH3:22])[N:4]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[CH:24]=2)[C:3]1=[O:33].C(O)(=[O:36])C.[Se](=O)=O>O1CCOCC1>[OH:36][CH2:22][C:5]1[N:4]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:30])([F:31])[F:32])[CH:24]=2)[C:3](=[O:33])[N:2]([CH3:1])[C:7](=[O:8])[C:6]=1[C:9]1[N:13]([C:14]2[CH:15]=[CH:16][C:17]([C:18]#[N:19])=[CH:20][CH:21]=2)[N:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 24007Selenium DioxideHCID 712514174-[5-[3,6-dimethyl-2,4-dioxo-1-(3-trifluoromethylphenyl)-1,2,3,4-tetrahydropyrimidin-5-yl]-1H-pyrazol-1-yl]benzonitrile

Product 1

HCID 901973724-(5-(6-(Hydroxymethyl)-3-methyl-2,4-dioxo-1-(3-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydropyrimidin-5-yl)-1H-pyrazol-1-yl)benzonitrile

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 4-[5-[3,6-dimethyl-2,4-dioxo-1-(3-trifluoromethylphenyl)-1,2,3,4-tetrahydropyrimidin-5-yl]-1H-pyrazol-1-yl]benzonitrile (prepared in Example 1) (50.0 mg) in dioxane (1.0 ml) were added acetic acid (0.5 ml) and selenium dioxide (74.0 mg) and the resulting mixture was stirred with heating under reflux for six hours. The reaction mixture was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate) to afford 4-[5-(6-hydroxymethyl)-3-methyl-2,4-dioxo-1-(3-trifluoromethylphenyl)-1,2,3,4-tetrahydropyrimidin-5-yl]-1H-pyrazol-1-yl]benzonitrile (3.7 mg).

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for six hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate)
  5. customto afford 4-[5-(6-hydroxymethyl)-3-methyl-2,4-dioxo-1-(3-trifluoromethylphenyl)-1,2,3,4-tetrahydropyrimidin-5-yl]-1H-pyrazol-1-yl]benzonitrile (3.7 mg)

Sources & evidence

ORD record
ord-c50c4c2082c54902947afe90aa4e8525
Source dataset
uspto-grants-2015_05
Patent number
US09040516B2

Reaction notes

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