Triethylsilane → HCID 178454101, compound

HRID 707260Notes

Reaction equation

HRID 707260 reaction equation
[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]

Participants

5

Reactant 2

HCID 12052TriethylsilaneHCID 178503401HCID 178503401, compound

Product 1

HCID 178454101HCID 178454101, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

  1. filtrationfiltered
  2. concentrationfiltrate concentrated

Sources & evidence

ORD record
ord-93149cffd59241ccbfb2f5190598ddec
Source dataset
uspto-grants-2015_11
Patent number
US09174992B2

Reaction notes

Loading…