Methanol → HCID 86723874, compound

HRID 576771Notes

Reaction equation

HRID 576771 reaction equation
C([O:8][C:9](=[O:43])[CH2:10][N:11]1[C:16](=[O:17])[C:15]([C:18]2[N:22]([C:23]3[CH:28]=[CH:27][C:26]([C:29]#[N:30])=[CH:25][CH:24]=3)[N:21]=[CH:20][CH:19]=2)=[C:14]([CH3:31])[N:13]([C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([C:38]([F:41])([F:40])[F:39])[CH:33]=2)[C:12]1=[O:42])C1C=CC=CC=1.CO>C(OCC)(=O)C.[Pd]>[C:29]([C:26]1[CH:27]=[CH:28][C:23]([N:22]2[C:18]([C:15]3[C:16](=[O:17])[N:11]([CH2:10][C:9]([OH:43])=[O:8])[C:12](=[O:42])[N:13]([C:32]4[CH:37]=[CH:36][CH:35]=[C:34]([C:38]([F:40])([F:41])[F:39])[CH:33]=4)[C:14]=3[CH3:31])=[CH:19][CH:20]=[N:21]2)=[CH:24][CH:25]=1)#[N:30]

Participants

5

Reactant 2

HCID 887MethanolHCID 86723875HCID 86723875, compound

Product 1

HCID 86723874HCID 86723874, compoundYield 111.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-[5-[1-(4-cyanophenyl)-1H-pyrazole-5-yl]-4-methyl-2,6-dioxo-3-(3-trifluoromethylphenyl)-2,3-dihydropyrimidin-1(6H)-yl]acetic acid benzyl ester (prepared in Example 6) (50.0 mg) in ethyl acetate (3.0 ml)/methanol (3.0 ml) was added 5% palladium/carbon (9.0 mg) and the resulting mixture was stirred at room temperature under hydrogen atmosphere for six hours. The reaction mixture was degassed and then filtered through Celite (trade mark) and then concentrated under reduced pressure to afford 2-[5-[1-(4-cyanophenyl)-1H-pyrazole-5-yl]-4-methyl-2,6-dioxo-3-(3-trifluoromethylphenyl)-2,3-dihydropyrimidin-1(6H)-yl]acetic acid (47.0 mg).

Workup

  1. customThe reaction mixture was degassed
  2. filtrationfiltered through Celite (trade mark)
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-471aad48ad4641a79a3e0ff6dd614cd7
Source dataset
uspto-grants-2015_05
Patent number
US09040516B2

Reaction notes

Loading…