HCID 52913736, compound → HCID 56933036, compound

HRID 594989Notes

Reaction equation

HRID 594989 reaction equation
[O:1]1[CH2:6][CH:5]=[C:4]([C:7]2[CH:8]=[C:9]([CH:27]=[CH:28][CH:29]=2)[CH2:10][N:11]2[C:15]3=[N:16][C:17]([NH:20][C:21]4[CH:22]=[N:23][N:24]([CH3:26])[CH:25]=4)=[N:18][CH:19]=[C:14]3[CH:13]=[N:12]2)[CH2:3][CH2:2]1>CO.[Pd]>[CH3:26][N:24]1[CH:25]=[C:21]([NH:20][C:17]2[N:16]=[C:15]3[N:11]([CH2:10][C:9]4[CH:27]=[CH:28][CH:29]=[C:7]([CH:4]5[CH2:5][CH2:6][O:1][CH2:2][CH2:3]5)[CH:8]=4)[N:12]=[CH:13][C:14]3=[CH:19][N:18]=2)[CH:22]=[N:23]1

Participants

4

Reactant 1

HCID 52913736HCID 52913736, compound

Product 1

HCID 56933036HCID 56933036, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

1-(3-(3,6-dihydro-2H-pyran-4-yl)benzyl)-N-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine was dissolved in methanol (8 mL) and palladium on carbon was added under an inert atmosphere. The reaction mixture was stirred overnight at rt under a hydrogen atmosphere. The mixture was filtered over Celite, then evaporated, and the residue was purified by preparative HPLC to afford the title compound (13 mg, 32 μmol, 38% over two steps). 1H NMR (d6-DMSO) δ 9.84 (s, 1H), 8.91 (s, 1H), 8.11-8.02 (m, 2H), 7.58 (s, 1H), 7.31-7.22 (m, 2H), 7.19-7.14 (m, 1H), 7.13-7.07 (m, 1H), 5.54 (s, 2H), 3.94-3.86 (m, 2H), 3.85 (s, 3H), 3.44-3.35 (m, 2H), 2.75-2.65 (m, 1H), 1.66-1.54 (m, 4H); LC-MS method B, (ES+) 390.2, RT=8.40 min.

Workup

  1. filtrationThe mixture was filtered over Celite
  2. customevaporated
  3. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-e03908921b32416eba39da0045f6948f
Source dataset
uspto-grants-2016_01
Patent number
US09242987B2

Reaction notes

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