Ethanol → 2-cyclopropyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (2-carbamoyl-1-cyclopropyl-2-methyl-propyl)-amide

HRID 446937ノート

反応式

HRID 446937 の反応式
[C:1]([C:3]([CH3:32])([CH3:31])[CH:4]([NH:8][C:9]([C:11]1[C:19]2[C:14](=[N:15][CH:16]=[C:17]([CH:20]3[CH2:22][CH2:21]3)[N:18]=2)[N:13]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28])[CH:12]=1)=[O:10])[CH:5]1[CH2:7][CH2:6]1)#[N:2].CC[OH:35]>O.[PtH]1([P](O[H]O[P]1(C)C)(C)C)[P](O)(C)C>[C:1]([C:3]([CH3:32])([CH3:31])[CH:4]([NH:8][C:9]([C:11]1[C:19]2[C:14](=[N:15][CH:16]=[C:17]([CH:20]3[CH2:22][CH2:21]3)[N:18]=2)[N:13]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:29])([CH3:28])[CH3:30])[CH:12]=1)=[O:10])[CH:5]1[CH2:6][CH2:7]1)(=[O:35])[NH2:2]

参加物

4

反応物 2

HCID 702EthanolHCID 670092382-cyclopropyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (2-cyano-1-cyclopropyl-2,2-dimethyl-ethyl)-amide

生成物 1

HCID 673888952-cyclopropyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (2-carbamoyl-1-cyclopropyl-2-methyl-propyl)-amide収率 64%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

To a solution of 2-cyclopropyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (2-cyano-1-cyclopropyl-2,2-dimethyl-ethyl)-amide (163 mg, 0.36 mmol) in EtOH (9 mL) and H2O (1 mL) was added [PtH(PMe2OH)(PMe2O)2H] (15 mg, 0.036 mmol). The reaction mixture was heated at reflux for 6 h. Additional catalyst (10 mg, 0.023 mmol) was added and heating was continued overnight. The reaction mixture was cooled to room temperature and concentrated. The residue was purified by SiO2 chromatography (50% to 100% EtOAc/hexanes) to provide 108 mg (64%) of 2-cyclopropyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (2-carbamoyl-1-cyclopropyl-2-methyl-propyl)-amide as a viscous colorless oil.

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 6 h
  3. temperatureheating
  4. concentrationconcentrated
  5. customThe residue was purified by SiO2 chromatography (50% to 100% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-3904d24b61364957814d8aa9ff5fe3a3
出典データセット
uspto-grants-2013_07
特許番号
US08481541B2

反応ノート

読み込み中…