Methoxymethyl-triphenylphosphonium chloride → HCID 86723914, 화합물

HRID 576812노트

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HRID 576812 반응식
[Cl-].COC[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(O[K])(C)(C)C.[CH2:30]([CH2:33][O:34][CH3:35])OC.C1(C)C=CC=CC=1.[CH3:43][C:44]1[N:49]([C:50]2[CH:55]=[CH:54][CH:53]=[C:52]([C:56]([F:59])([F:58])[F:57])[CH:51]=2)[C:48](=[O:60])[N:47]([C@H:61](C)[CH:62]=O)[C:46](=[O:65])[C:45]=1[C:66]1[N:70]([C:71]2[CH:78]=[CH:77][C:74]([C:75]#[N:76])=[CH:73][CH:72]=2)[N:69]=[CH:68][CH:67]=1>C(OCC)(=O)C.O>[CH3:35][O:34][CH:33]=[CH:30][C@H:61]([N:47]1[C:46](=[O:65])[C:45]([C:66]2[N:70]([C:71]3[CH:72]=[CH:73][C:74]([C:75]#[N:76])=[CH:77][CH:78]=3)[N:69]=[CH:68][CH:67]=2)=[C:44]([CH3:43])[N:49]([C:50]2[CH:55]=[CH:54][CH:53]=[C:52]([C:56]([F:59])([F:57])[F:58])[CH:51]=2)[C:48]1=[O:60])[CH3:62]

참가 물질

7

반응물 4

HCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 69178531Toluene dimethoxyethaneHCID 71514795HCID 71514795, 화합물HCID 178418922HCID 178418922, 화합물

생성물 1

HCID 86723914HCID 86723914, 화합물

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매

실험 절차

To (methoxymethyl)triphenylphoshonium chloride (1.74 g) and tertiary-butoxy potassium (853 mg) was added at 0° C. glyme/toluene (10 ml/10 ml) and the resulting mixture was stirred for fifteen minutes. To the reaction mixture was added at 0° C. (R)-4-(5-(6-methyl-2,4-dioxo-3-(1-oxopropane-2-yl)-1-(3-trifluoromethylphenyl)-1,2,3,4-tetrahydropyrimidin-5-yl)-1H-pyrazol-1-yl)benzonitrile (prepared in Example 373) (500 mg) and the resulting mixture was stirred at room temperature for fifteen hours. To the reaction mixture was added water (20 ml) followed by an addition of ethyl acetate (30 ml×2) such that the intended products were extracted into an organic layer. The organic layer was washed with saturated saline (20 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 (R)-4-(5-(3-(4-methoxy-3-buten-2-yl)-6-methyl-2,4-dioxo-1-(3-trifluoromethylphenyl)-1,2,3,4-tetrahydropyrimidin-5-yl)-1H-pyrazol-1-yl)benzonitrile (350 mg). UPLC/MS 522 (M+H)/1.00 min. (measurement condition 9)

후처리

  1. stirringthe resulting mixture was stirred at room temperature for fifteen hours
  2. extractionwere extracted into an organic layer
  3. washThe organic layer was washed with saturated saline (20 ml)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate)

출처 및 근거

ORD 기록
ord-9eb6db23645f4d6c93bdda4035084079
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09040516B2

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