Ammonium Chloride → 4-(5-(6-(dibromomethyl)-3-methyl-2,4-dioxo-1-(3-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydropyrimidin-5-yl)-1H-pyrazol-1-yl)benzonitrile
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CN1C(=O)C(C2N(C3C=CC(C#N)=CC=3)N=CC=2)=C(C)N(C2C=CC=C(C(F)(F)F)C=2)C1=O.C[Si](C)(C)[N-][Si](C)(C)C.[Li+].[Br:44]N1C(=O)CCC1=O.[Cl-].[NH4+].[Br:54][CH2:55][C:56]1[N:61]([C:62]2[CH:67]=[CH:66][CH:65]=[C:64]([C:68]([F:71])([F:70])[F:69])[CH:63]=2)[C:60](=[O:72])[N:59]([CH3:73])[C:58](=[O:74])[C:57]=1[C:75]1[N:79]([C:80]2[CH:87]=[CH:86][C:83]([C:84]#[N:85])=[CH:82][CH:81]=2)[N:78]=[CH:77][CH:76]=1>O1CCCC1>[Br:54][CH:55]([Br:44])[C:56]1[N:61]([C:62]2[CH:67]=[CH:66][CH:65]=[C:64]([C:68]([F:71])([F:70])[F:69])[CH:63]=2)[C:60](=[O:72])[N:59]([CH3:73])[C:58](=[O:74])[C:57]=1[C:75]1[N:79]([C:80]2[CH:81]=[CH:82][C:83]([C:84]#[N:85])=[CH:86][CH:87]=2)[N:78]=[CH:77][CH:76]=1참가 물질
반응물 5
HCID 25517Ammonium Chloride
HCID 67184N-bromobutanimide
HCID 2733832Lithium Hexamethyldisilazide
HCID 712514174-[5-[3,6-dimethyl-2,4-dioxo-1-(3-trifluoromethylphenyl)-1,2,3,4-tetrahydropyrimidin-5-yl]-1H-pyrazol-1-yl]benzonitrile
HCID 901970994-(5-(6-(Bromomethyl)-3-methyl-2,4-dioxo-1-(3-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydropyrimidin-5-yl)-1H-pyrazol-1-yl)benzonitrile생성물 1
시약·촉매·용매 1
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- 온도
- 0 °C
실험 절차
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) (30.0 mg) in tetrahydrofuran (1.0 ml) was added at 0° C. lithium hexamethyldisilazide (0.1 ml: 1M tetrahydrofuran solution) followed by an addition of N-bromosuccinimide (14.4 mg), and the resulting mixture was stirred at 0° C. for a half hour. To the reaction mixture was added saturated aqueous ammonium chloride solution (5 ml) and the 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. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate) to afford 4-[5-(6,6-dibromomethyl)-3-methyl-2,4-dioxo-1-(3-trifluoromethylphenyl)-1,2,3,4-tetrahydropyrimidin-5-yl]-1H-pyrazol-1-yl]benzonitrile (5.4 mg) and 4-[5-(6-bromomethyl)-3-methyl-2,4-dioxo-1-(3-trifluoromethylphenyl)-1,2,3,4-tetrahydropyrimidin-5-yl]-1H-pyrazol-1-yl]benzonitrile (6.9 mg). 4-(5-(6-(Bromomethyl)-3-methyl-2,4-dioxo-1-(3-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydropyrimidin-5-yl)-1H-pyrazol-1-yl)benzonitrile:
후처리
- extractionthe 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
- customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate)
- customto afford 4-[5-(6,6-dibromomethyl)-3-methyl-2,4-dioxo-1-(3-trifluoromethylphenyl)-1,2,3,4-tetrahydropyrimidin-5-yl]-1H-pyrazol-1-yl]benzonitrile (5.4 mg) and 4-[5-(6-bromomethyl)-3-methyl-2,4-dioxo-1-(3-trifluoromethylphenyl)-1,2,3,4-tetrahydropyrimidin-5-yl]-1H-pyrazol-1-yl]benzonitrile (6.9 mg)
출처 및 근거
- ORD 기록
- ord-66657737863e4c05a4b86bbbdfebac6b
- 출처 데이터셋
- uspto-grants-2015_05
- 특허 번호
- US09040516B2
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