tert-butyl 4-((9-methyl-2-(2-methyl-1H-benzo[d]imidazol-1-yl)-6-morpholino-9H-purin-8-yl)methylene)piperidine-1-carboxylate → tert-butyl 4-((9-methyl-2-(2-methyl-1H-benzo[d]imidazol-1-yl)-6-morpholino-9H-purin-8-yl)methyl)piperidine-1-carboxylate

HRID 1923215Notes

Reaction equation

HRID 1923215 reaction equation
[CH3:1][N:2]1[C:10]([CH:11]=[C:12]2[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]2)=[N:9][C:8]2[C:3]1=[N:4][C:5]([N:31]1[C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=3[N:33]=[C:32]1[CH3:40])=[N:6][C:7]=2[N:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1>C(O)C.[Pd]>[CH3:1][N:2]1[C:10]([CH2:11][CH:12]2[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]2)=[N:9][C:8]2[C:3]1=[N:4][C:5]([N:31]1[C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=3[N:33]=[C:32]1[CH3:40])=[N:6][C:7]=2[N:25]1[CH2:26][CH2:27][O:28][CH2:29][CH2:30]1

Participants

4

Reactant 1

HCID 59605768tert-butyl 4-((9-methyl-2-(2-methyl-1H-benzo[d]imidazol-1-yl)-6-morpholino-9H-purin-8-yl)methylene)piperidine-1-carboxylate

Product 1

HCID 59605471tert-butyl 4-((9-methyl-2-(2-methyl-1H-benzo[d]imidazol-1-yl)-6-morpholino-9H-purin-8-yl)methyl)piperidine-1-carboxylateYield 90.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of tert-butyl 4-((9-methyl-2-(2-methyl-1H-benzo[d]imidazol-1-yl)-6-morpholino-9H-purin-8-yl)methylene)piperidine-1-carboxylate (0.39 g, 0.729 mmol) and Pd/C (10 wt %, 0.1 g) in ethanol (15 mL) was stirred under a hydrogen atmosphere (balloon) at room temperature for 18 hours. The reaction mixture was then filtered through celite and concentrated. The crude product was purified by flash chromatography (0-5% MeOH in DCM) to give the title compound (0.36 g, 90%). LCMS m/z: 547.2 (MH+)

Workup

  1. filtrationThe reaction mixture was then filtered through celite
  2. concentrationconcentrated
  3. customThe crude product was purified by flash chromatography (0-5% MeOH in DCM)

Sources & evidence

ORD record
ord-9a71a7cc32de4f8fa2ba45deccb6e28c
Source dataset
uspto-grants-2012_05
Patent number
US08173650B2

Reaction notes

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