HCID 67494607, compound → HCID 66733702, compound

HRID 2047144Notes

Reaction equation

HRID 2047144 reaction equation
C([O:8][C@@H:9]([C:11]1[O:15][C:14]([N:16]2[CH2:21][CH2:20][CH:19]([C:22]3[CH:27]=[C:26]([N:28]([CH2:37][O:38][CH2:39][CH2:40][Si:41]([CH3:44])([CH3:43])[CH3:42])[CH2:29][O:30][CH2:31][CH2:32][Si:33]([CH3:36])([CH3:35])[CH3:34])[N:25]4[N:45]=[CH:46][C:47]([C:48]5[CH:49]=[N:50][C:51]([C:54]6[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=6)=[CH:52][CH:53]=5)=[C:24]4[N:23]=3)[CH2:18][CH2:17]2)=[N:13][N:12]=1)[CH3:10])C1C=CC=CC=1>CO.[OH-].[OH-].[Pd+2]>[CH3:43][Si:41]([CH3:42])([CH3:44])[CH2:40][CH2:39][O:38][CH2:37][N:28]([CH2:29][O:30][CH2:31][CH2:32][Si:33]([CH3:36])([CH3:35])[CH3:34])[C:26]1[N:25]2[N:45]=[CH:46][C:47]([C:48]3[CH:49]=[N:50][C:51]([C:54]4[CH:55]=[CH:56][CH:57]=[CH:58][CH:59]=4)=[CH:52][CH:53]=3)=[C:24]2[N:23]=[C:22]([CH:19]2[CH2:18][CH2:17][N:16]([C:14]3[O:15][C:11]([C@H:9]([OH:8])[CH3:10])=[N:12][N:13]=3)[CH2:21][CH2:20]2)[CH:27]=1

Participants

4

Reactant 1

HCID 67494607HCID 67494607, compound

Product 1

HCID 66733702HCID 66733702, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A mixture of (R)-5-(1-(5-(1-(benzyloxy)ethyl)-1,3,4-oxadiazol-2-yl)piperidin-4-yl)-3-(6-phenylpyridin-3-yl)-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)pyrazolo[1,5-a]pyrimidin-7-amine (105 mg), 20% Pd(OH)2/C (150 mg) in MeOH (4 mL) was stirred under hydrogen (60 psi) overnight. After filtration, washing with EtOAc 4 times and concentration in vacuo the residue was purified on silica gel. Elution with EtOAc/Hexanes (0-100%) gave the title compound (32 mg, 43%).

Workup

  1. filtrationAfter filtration
  2. washwashing with EtOAc 4 times and concentration in vacuo the residue
  3. customwas purified on silica gel
  4. washElution with EtOAc/Hexanes (0-100%)

Sources & evidence

ORD record
ord-2229b58b38194ca9aef86b992d63abe7
Source dataset
uspto-grants-2013_11
Patent number
US08591943B2

Reaction notes

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