Triethylsilane → HCID 178454101、化合物

HRID 707260ノート

反応式

HRID 707260 の反応式
[C:1]([O:5][C:6](=[O:26])[NH:7][C@H:8]1[CH2:11][C@H:10]([N:12]2[C:16]3[N:17]=[C:18](SC)[N:19]=[CH:20][C:15]=3[C:14]([CH3:24])([CH3:23])[C:13]2=[O:25])[CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C([SiH](CC)CC)C>O1CCCC1.[Pd]>[C:1]([O:5][C:6](=[O:26])[NH:7][C@H:8]1[CH2:9][C@H:10]([N:12]2[C:16]3[N:17]=[CH:18][N:19]=[CH:20][C:15]=3[C:14]([CH3:24])([CH3:23])[C:13]2=[O:25])[CH2:11]1)([CH3:4])([CH3:2])[CH3:3]

参加物

5

反応物 2

HCID 12052TriethylsilaneHCID 178503401HCID 178503401、化合物

生成物 1

HCID 178454101HCID 178454101、化合物

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of tert-butyl(trans-3-(5,5-dimethyl-2-(methylthio)-6-oxo-5H-pyrrolo[2,3-d]pyrimidin-7(6H)-yl)cyclobutyl)carbamate, INTERMEDIATE 63, (0.9 g, 2.378 mmol) in dry tetrahydrofuran (10 mL) was added cautiously palladium 10 wt. % on activated carbon (0.051 ml, 0.476 mmol) followed by triethylsilane (3.04 ml, 19.02 mmol). The mixture was stirred for 15 minutes under nitrogen atmosphere, filtered, and filtrate concentrated to give tert-butyl(trans-3-(5,5-dimethyl-6-oxo-5H-pyrrolo[2,3-d]pyrimidin-7(6H)-yl)cyclobutyl)carbamate. The crude tert-butyl(trans-3-(5,5-dimethyl-6-oxo-5H-pyrrolo[2,3-d]pyrimidin-7(6H)-yl)cyclobutyl)carbamate was redissolved in dioxane (10 mL) and treated with 4N HCl in dioxane (10 mL). After 30 minutes the reaction mixture was evaporated to dryness under reduced pressure to give the desired crude product 7-(trans-3-aminocyclobutyl)-5,5-dimethyl-5H-pyrrolo[2,3-d]pyrimidin-6(7H)-one hydrochloride (0.55 g, 2.047 mmol, 86% yield). The product was used in next step without further purification. m/z: 233.0 (M+1-HCl).

後処理

  1. filtrationfiltered
  2. concentrationfiltrate concentrated

出典と根拠

ORDレコード
ord-93149cffd59241ccbfb2f5190598ddec
出典データセット
uspto-grants-2015_11
特許番号
US09174992B2

反応ノート

読み込み中…