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(2S)-2-(1-(2-Chlorophenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy)-3-cyclobutoxy-N-(5-methylpyrazin-2-yl)propanamide → (S)-3-cyclobutoxy-N-(5-methylpyrazin-2-yl)-2-(1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy)propanamide

HRID 1098008
Notes
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Reaction equation

HRID 1098008 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]2=[N:13][CH:14]=[N:15][C:16]([O:17][C@@H:18]([CH2:29][O:30][CH:31]3[CH2:34][CH2:33][CH2:32]3)[C:19]([NH:21][C:22]3[CH:27]=[N:26][C:25]([CH3:28])=[CH:24][N:23]=3)=[O:20])=[C:11]2[CH:10]=[N:9]1>[Pd].C(O)C>[CH:31]1([O:30][CH2:29][C@H:18]([O:17][C:16]2[N:15]=[CH:14][N:13]=[C:12]3[N:8]([C:3]4[CH:4]=[CH:5][CH:6]=[CH:7][CH:2]=4)[N:9]=[CH:10][C:11]=23)[C:19]([NH:21][C:22]2[CH:27]=[N:26][C:25]([CH3:28])=[CH:24][N:23]=2)=[O:20])[CH2:34][CH2:33][CH2:32]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 1

HCID 59279550(2S)-2-(1-(2-Chlorophenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy)-3-cyclobutoxy-N-(5-methylpyrazin-2-yl)propanamide

Product 1

HCID 59279532(S)-3-cyclobutoxy-N-(5-methylpyrazin-2-yl)-2-(1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy)propanamideYield 17.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 702EthanolSolvent

Procedure

(2S)-2-(1-(2-Chlorophenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy)-3-cyclobutoxy-N-(5-methylpyrazin-2-yl)propanamide (Example 156) (102 mg, 0.21 mmol) and 10% palladium on carbon (25 mg, 0.02 mmol) in ethanol (20 mL) were stirred under an atmosphere of hydrogen for 16 hours. The suspension was filtered through celite. 10% Palladium on carbon (25 mg, 0.02 mmol) was added and the resulting suspension was stirred under an atmosphere of hydrogen for 24 hours. The reaction mixture was filtered through celite and evaporated. The residue was purified by flash silica chromatography, eluting with 0 to 50% ethyl acetate in isohexane to afford the product (16.0 mg, 16.9%).

Workup

  1. filtrationThe suspension was filtered through celite
  2. filtrationThe reaction mixture was filtered through celite
  3. customevaporated
  4. customThe residue was purified by flash silica chromatography
  5. washeluting with 0 to 50% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-2652b0f8eb70403b8cbd4317cbec0728
Source dataset
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08143263B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes