7-[(1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethyl]-4-chloro-7H-pyrrolo[2,3-d]pyrimidine → 7-[(1S)-2-{[tert-Butyl(dimethyl)silyl]oxy}-1-methylethyl]-7H-pyrrolo[2,3-d]pyrimidine

HRID 82144

Reaction equation

HRID 82144 reaction equation
[Si:1]([O:8][CH2:9][C@@H:10]([N:12]1[C:16]2[N:17]=[CH:18][N:19]=[C:20](Cl)[C:15]=2[CH:14]=[CH:13]1)[CH3:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>C(O)C.N.[Pd]>[Si:1]([O:8][CH2:9][C@@H:10]([N:12]1[C:16]2[N:17]=[CH:18][N:19]=[CH:20][C:15]=2[CH:14]=[CH:13]1)[CH3:11])([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:2])[CH3:3]

Participants

5

Reactant 1

HCID 866720787-[(1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethyl]-4-chloro-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 708176697-[(1S)-2-{[tert-Butyl(dimethyl)silyl]oxy}-1-methylethyl]-7H-pyrrolo[2,3-d]pyrimidineYield 94%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 222AmmoniaSolventHCID 702EthanolSolvent

Procedure

Palladium (10% on carbon, 18 g) was added to 7-[(1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethyl]-4-chloro-7H-pyrrolo[2,3-d]pyrimidine (182 g, 558 mmol) (see Preparation 1) in ethanol (900 mL) and concentrated ammonia solution (100 mL) and hydrogenated (60 psi, 20° C.) for 18 hours. The reaction mixture was filtered through Arbocel™ and the filtrate was evaporated in vacuo. Diethyl ether (300 mL) was added to the residue and the mixture was filtered. The filtrate was evaporated in vacuo to afford the title compound as an orange oil in 94% yield, 162.7 g.

Workup

  1. filtrationThe reaction mixture was filtered through Arbocel™
  2. customthe filtrate was evaporated in vacuo
  3. additionDiethyl ether (300 mL) was added to the residue
  4. filtrationthe mixture was filtered
  5. customThe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-4597911af295450aaca7933c8a0f5f58
Source dataset
uspto-grants-2014_09
Patent number
US08846698B2

Linked notes

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