3-[2-(2-Ethylbenzoimidazol-1-yl)-9-methyl-6-morpholin-4-yl-9H-purin-8-ylmethylene]azetidine-1-carboxylic acid tert-butyl ester → 3-[2-(2-Ethylbenzoimidazol-1-yl)-9-methyl-6-morpholin-4-yl-9H-purin-8-ylmethyl]azetidine-1-carboxylic acid tert-butyl ester

HRID 1923228Notes

Reaction equation

HRID 1923228 reaction equation
[CH3:1][N:2]1[C:10]([CH:11]=[C:12]2[CH2:15][N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:13]2)=[N:9][C:8]2[C:3]1=[N:4][C:5]([N:29]1[C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=3[N:31]=[C:30]1[CH2:38][CH3:39])=[N:6][C:7]=2[N:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1>C(O)C.[Pd]>[CH3:1][N:2]1[C:10]([CH2:11][CH:12]2[CH2:13][N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:15]2)=[N:9][C:8]2[C:3]1=[N:4][C:5]([N:29]1[C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=3[N:31]=[C:30]1[CH2:38][CH3:39])=[N:6][C:7]=2[N:23]1[CH2:24][CH2:25][O:26][CH2:27][CH2:28]1

Participants

4

Reactant 1

HCID 596052023-[2-(2-Ethylbenzoimidazol-1-yl)-9-methyl-6-morpholin-4-yl-9H-purin-8-ylmethylene]azetidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 596056563-[2-(2-Ethylbenzoimidazol-1-yl)-9-methyl-6-morpholin-4-yl-9H-purin-8-ylmethyl]azetidine-1-carboxylic acid tert-butyl esterYield 58%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of tert-butyl 3-((9-methyl-2-(2-ethyl-1H-benzo[d]imidazol-1-yl)-6-morpholino-9H-purin-8-yl)methylene)azetidine-1-carboxylate (1.1 g, 2.1 mmol) and Pd/C (10 wt %, 0.4 g) in ethanol (25 mL) was stirred under a hydrogen atmosphere (balloon) at room temperature for 24 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 (0.64 g, 58%). 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-10139fe9b842409a9daf7a5c91587e19
Source dataset
uspto-grants-2012_05
Patent number
US08173650B2

Reaction notes

Loading…