HCID 68376752, compound → HCID 68376883, compound

HRID 594977Notes

Reaction equation

HRID 594977 reaction equation
C([O:8][CH2:9][CH2:10][O:11][C:12]1[CH:13]=[C:14]([CH:32]=[CH:33][CH:34]=1)[CH2:15][N:16]1[C:20]2=[N:21][C:22]([NH:25][C:26]3[CH:27]=[N:28][N:29]([CH3:31])[CH:30]=3)=[N:23][CH:24]=[C:19]2[CH:18]=[N:17]1)C1C=CC=CC=1>CO.[Pd]>[CH3:31][N:29]1[CH:30]=[C:26]([NH:25][C:22]2[N:21]=[C:20]3[N:16]([CH2:15][C:14]4[CH:13]=[C:12]([CH:34]=[CH:33][CH:32]=4)[O:11][CH2:10][CH2:9][OH:8])[N:17]=[CH:18][C:19]3=[CH:24][N:23]=2)[CH:27]=[N:28]1

Participants

4

Reactant 1

HCID 68376752HCID 68376752, compound

Product 1

HCID 68376883HCID 68376883, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

1-(3-(2-(benzyloxy)ethoxy)benzyl)-N-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine (39 mg, 86 μmol) was dissolved in 2 mL methanol then palladium on carbon added under an inert atmosphere and the reaction mixture stirred overnight at rt under an hydrogen atmosphere. The reaction mixture was filtered through Celite and evaporated to afford the title compound after purification by preparative HPLC. 1H NMR (d6-DMSO) δ 9.85 (s, 1H), 8.92 (s, 1H), 8.11-7.97 (m, 2H), 7.56 (s, 1H), 7.23 (t, J=8.0 Hz, 1H), 6.95-6.74 (m, 3H), 5.52 (s, 2H), 4.81 (t, J=5.5 Hz, 1H), 3.90 (t, J=5.0 Hz, 2H), 3.83 (s, 3H), 3.65 (m, 2H); LC-MS method B, (ES+) 366.0, RT=6.64 min.

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. customevaporated

Sources & evidence

ORD record
ord-bed45516c2804959860ed6007bc4f4e1
Source dataset
uspto-grants-2016_01
Patent number
US09242987B2

Reaction notes

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