Water → HCID 86723870, compound

HRID 576768Notes

Reaction equation

C[O:2][CH:3](OC)[CH2:4][N:5]1[C:10](=[O:11])[C:9]([C:12]2[N:16]([C:17]3[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[CH:19][CH:18]=3)[N:15]=[CH:14][CH:13]=2)=[C:8]([CH3:25])[N:7]([C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:35])([F:34])[F:33])[CH:27]=2)[C:6]1=O.O.FC(F)(F)C(O)=O.[OH-].[Na+]>O1CCCC1>[CH3:25][C:8]1[N:7]([C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:35])([F:34])[F:33])[CH:27]=2)[CH2:6][N:5]([CH2:4][CH:3]=[O:2])[C:10](=[O:11])[C:9]=1[C:12]1[N:16]([C:17]2[CH:18]=[CH:19][C:20]([C:21]#[N:22])=[CH:23][CH:24]=2)[N:15]=[CH:14][CH:13]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 4-[5-[3-(2,2-dimethoxyethyl)-6-methyl-2,4-dioxo-1-(3-trifluoromethylphenyl)-1,2,3,4-tetrahydropyrimidin-5-yl]-1H-pyrazol-1-yl]benzonitrile (prepared in Example 7) (10.0 mg) in tetrahydrofuran (0.5 ml)/water (0.1 mL) was added trifluoroacetic acid (40 μl) and the resulting mixture was stirred at 100° C. for three hours. The reaction mixture was neutralized with aqueous sodium hydroxide solution, and thereto was added water and the resulting mixture was extracted with ethyl acetate (10 ml×2). The organic layer was washed with saturated saline (10 ml), dried over anhydrous sodium sulfate and then concentrated under reduced pressure to afford 4-[5-[6-methyl-4-oxo-3-(2-oxoethyl)-1-(3-trifluoromethylphenyl)-1,2,3,4-tetrahydropyrimidin-5-yl]-1H-pyrazol-1-yl]benzonitrile (9.1 mg).

Workup

extractionthe resulting mixture was extracted with ethyl acetate (10 ml×2)
washThe organic layer was washed with saturated saline (10 ml)
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-e862e878663a4874b9b95c0fd0369d8d
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09040516B2

Reaction notes

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