Methoxymethyl-triphenylphosphonium chloride → HCID 86723914、化合物

HRID 576812ノート

反応式

HRID 576812 の反応式
[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]

参加物

7

反応物 4

HCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 69178531Toluene dimethoxyethaneHCID 71514795HCID 71514795、化合物HCID 178418922HCID 178418922、化合物

生成物 1

HCID 86723914HCID 86723914、化合物

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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)

後処理

  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)

出典と根拠

ORDレコード
ord-9eb6db23645f4d6c93bdda4035084079
出典データセット
uspto-grants-2015_05
特許番号
US09040516B2

反応ノート

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