Triphenylphosphine → tert-butyl 3-((4-amino-3-((3,5-dimethoxyphenyl)ethynyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)pyrrolidine-1-carboxylate

HRID 516149ノート

反応式

HRID 516149 の反応式
CC(OC(/N=N/C(OC(C)C)=O)=O)C.[CH3:15][O:16][C:17]1[CH:18]=[C:19]([C:25]#[C:26][C:27]2[C:35]3[C:30](=[N:31][CH:32]=[N:33][C:34]=3[NH2:36])[NH:29][N:28]=2)[CH:20]=[C:21]([O:23][CH3:24])[CH:22]=1.[C:37]([N:44]1[CH2:48][CH2:47][CH:46]([CH2:49]O)[CH2:45]1)([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[NH2:36][C:34]1[N:33]=[CH:32][N:31]=[C:30]2[N:29]([CH2:49][CH:46]3[CH2:47][CH2:48][N:44]([C:37]([O:39][C:40]([CH3:41])([CH3:43])[CH3:42])=[O:38])[CH2:45]3)[N:28]=[C:27]([C:26]#[C:25][C:19]3[CH:18]=[C:17]([O:16][CH3:15])[CH:22]=[C:21]([O:23][CH3:24])[CH:20]=3)[C:35]=12

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 5237175tert-Butyl 3-(hydroxymethyl)pyrrolidine-1-carboxylateHCID 5363146Diisopropyl azodicarboxylateHCID 178489940HCID 178489940、化合物

生成物 1

HCID 89870802tert-butyl 3-((4-amino-3-((3,5-dimethoxyphenyl)ethynyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)pyrrolidine-1-carboxylate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

DIAD (197 μl) was added to a suspension of 3-((3,5-dimethoxyphenyl)ethynyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (148 mg) obtained in Example 1 (Step 1), N-Boc-3-hydroxymethylpyrrolidine (154 mg), polymer supported triphenylphosphine (up to 3.0 mmol/g, 334 mg) in THF (5.0 ml), followed by stirring at room temperature for 3 hours. The insoluble matter was filtered out, and the solvent was distilled off under reduced pressure. The resulting residue was purified by basic silica gel column chromatography (developing solvent: hexane/ethyl acetate) to obtain the title compound as a colorless, amorphous substance (94.5 mg). Physical properties: m/z [M+H]+ 479.1

後処理

  1. filtrationThe insoluble matter was filtered out
  2. distillationthe solvent was distilled off under reduced pressure
  3. customThe resulting residue was purified by basic silica gel column chromatography (developing solvent: hexane/ethyl acetate)

出典と根拠

ORDレコード
ord-2a7e46a768fa4cbd8bd7d7a99f47d6ff
出典データセット
uspto-grants-2015_08
特許番号
US09108973B2

反応ノート

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