HCID 59553890, compound → 3-(1-(3,4-difluorophenyl)propan-2-yl)-2-(3-hydroxypyridin-2-yl)-5-(trifluoromethyl)pyrido[4,3-d]pyrimidin-4(3H)-one

HRID 1170928Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([CH2:9][CH:10]([N:12]2[C:17](=[O:18])[C:16]3[C:19]([C:23]([F:26])([F:25])[F:24])=[N:20][CH:21]=[CH:22][C:15]=3[NH:14][CH:13]2[C:27]2[C:32]([OH:33])=[CH:31][CH:30]=[CH:29][N:28]=2)[CH3:11])[CH:5]=[CH:6][C:7]=1[F:8]>CC(C)CC(=O)C.[O-2].[O-2].[Mn+4]>[F:1][C:2]1[CH:3]=[C:4]([CH2:9][CH:10]([N:12]2[C:17](=[O:18])[C:16]3[C:19]([C:23]([F:24])([F:25])[F:26])=[N:20][CH:21]=[CH:22][C:15]=3[N:14]=[C:13]2[C:27]2[C:32]([OH:33])=[CH:31][CH:30]=[CH:29][N:28]=2)[CH3:11])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

Conditions

Temperature: 90 °C

Procedure

3-(1-(3,4-difluorophenyl)propan-2-yl)-2-(3-hydroxypyridin-2-yl)-5-(trifluoromethyl)-2,3-dihydropyrido[4,3-d]pyrimidin-4(1H)-one (5.90 g, 12.7 mmol) was dissolved in 500 mL of 4-methyl-2-pentanone. To this solution, manganese dioxide was added (16.6 g, 191 mmol) and the mixture was heated to 90° C. for 1 hour. The reaction was cooled, filtered through Celite and washed with CH2CL2. The filtrate was collected and concentrated in vacuo as a yellow solid which was purified by silica gel chromatography to afford the racemic mixture 3-(1-(3,4-difluorophenyl)propan-2-yl)-2-(3-hydroxypyridin-2-yl)-5-(trifluoromethyl)pyrido[4,3-d]pyrimidin-4(3H)-one.

Workup

temperatureThe reaction was cooled
filtrationfiltered through Celite
washwashed with CH2CL2
customThe filtrate was collected
concentrationconcentrated in vacuo as a yellow solid which
customwas purified by silica gel chromatography

Sources & evidence

ORD record: ord-be7f6bd3f1744c9fa47c00b385b9c53e
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07829572B2

Reaction notes

Loading…