benzyl(4-(((tert-butyldimethylsilyl)oxy)methyl)-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridin-6-yl)carbamate → 4-(((tert-butyldimethylsilyl)oxy)methyl)-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridin-6-amine

HRID 588206Notes

Reaction equation

HRID 588206 reaction equation
C(OC(=O)[NH:10][C:11]1[N:16]=[C:15]([CH2:17][O:18][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20])[C:14]2[C:26]([O:48][CH3:49])=[N:27][N:28]([C:29]([C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:13]=2[CH:12]=1)C1C=CC=CC=1>C(OCC)(=O)C.CO.[Pd]>[Si:19]([O:18][CH2:17][C:15]1[C:14]2[C:26]([O:48][CH3:49])=[N:27][N:28]([C:29]([C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)([C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=3)[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:13]=2[CH:12]=[C:11]([NH2:10])[N:16]=1)([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:20])[CH3:21]

Participants

5

Reactant 1

HCID 123992626benzyl(4-(((tert-butyldimethylsilyl)oxy)methyl)-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridin-6-yl)carbamate

Product 1

HCID 1317344314-(((tert-butyldimethylsilyl)oxy)methyl)-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridin-6-amineYield 82.5%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a 50 mL round bottom flask charged with crude benzyl(4-(((tert-butyldimethylsilyl)oxy)methyl)-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridin-6-yl)carbamate (199 mg, 0.291 mmol) in ethyl acetate (10 ml) and methanol (5 ml) was added palladium on carbon (61.8 mg, 0.058 mmol). The flask was evacuated and back-filled with hydrogen gas using an attached balloon. This procedure was attempted a further two times. The reaction mixture was stirred under a hydrogen atmosphere at room temperature for 16 h. The palladium was filtered off by passing the reaction mixture through celite and washing through with methanol (20 mL). The volatiles were removed in vacuo to afford crude 4-(((tert-butyldimethylsilyl)oxy)methyl)-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridin-6-amine (132 mg, 0.240 mmol, 82% yield) as a yellow oil. The product was carried forward without purification. MS: [M+H]+ m/z 551.

Workup

  1. customThe flask was evacuated
  2. additionback-filled with hydrogen gas
  3. filtrationThe palladium was filtered off
  4. washwashing through with methanol (20 mL)
  5. customThe volatiles were removed in vacuo

Sources & evidence

ORD record
ord-2a4f2b8d8c77405c98e771f8efcb53b6
Source dataset
uspto-grants-2016_01
Patent number
US09226922B2

Reaction notes

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