Triethylsilane → HCID 178454101, 화합물

HRID 707260노트

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HRID 707260 반응식
[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]

참가 물질

5

반응물 2

HCID 12052TriethylsilaneHCID 178503401HCID 178503401, 화합물

생성물 1

HCID 178454101HCID 178454101, 화합물

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  1. filtrationfiltered
  2. concentrationfiltrate concentrated

출처 및 근거

ORD 기록
ord-93149cffd59241ccbfb2f5190598ddec
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09174992B2

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