4-chloro-1-(1-phenyl-1H-benzoimidazol-2-ylmethyl)-1H-Pyrazolo[3,4-d]pyrimidin-6-ylamine → HCID 60161898, compound

HRID 243331Notes

Reaction equation

HRID 243331 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH2:8])[N:5]=[C:4]2[N:9]([CH2:12][C:13]3[N:17]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[C:16]4[CH:24]=[CH:25][CH:26]=[CH:27][C:15]=4[N:14]=3)[N:10]=[CH:11][C:3]=12>CO.[Pd]>[C:18]1([N:17]2[C:16]3[CH:24]=[CH:25][CH:26]=[CH:27][C:15]=3[N:14]=[C:13]2[CH2:12][N:9]2[C:4]3=[N:5][C:6]([NH2:8])=[N:7][CH:2]=[C:3]3[CH:11]=[N:10]2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 1

HCID 866688834-chloro-1-(1-phenyl-1H-benzoimidazol-2-ylmethyl)-1H-Pyrazolo[3,4-d]pyrimidin-6-ylamine

Product 1

HCID 60161898HCID 60161898, compoundYield 15%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 4-chloro-1-(1-phenyl-1H-benzoimidazol-2-ylmethyl)-1H-Pyrazolo[3,4-d]pyrimidin-6-ylamine (1.5 g, 4 mmol) and Pd/C (0.3 g) in MeOH was stirred with H2 40 psi at 50° C. overnight. The mixture was filtered, and the filtrate was concentrated in vacuo. The residue was purified by P-TLC to give 157 (200 mg, yield 15%) as white solid. LCMS (ESI), M+H+=340.14. 1HNMR (400 MHz, DMSO) δ 5.0374 (s, 2H), 5.597 (s, 2H), 7.015 (s, 1H), 7.152-7.211 (m, 5H), 7.309-7.327 (m, 3H), 7.746 (s, 2H), 8.567 (s, 1H)

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified by P-TLC

Sources & evidence

ORD record
ord-16bf9b98a491413ead3b48599ca6c398
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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