Ethyl Acetate → 1-{1-[3-(2,4-Dimethoxy-pyrimidin-5-yl)-phenyl]-1H-benzoimidazol-5-yl}-ethylamine

HRID 2262747Notes

Reaction equation

HRID 2262747 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]([O:9][CH3:10])[C:6]([C:11]2[CH:12]=[C:13]([N:17]3[C:21]4[CH:22]=[CH:23][C:24]([CH:26]([NH:28]C=O)[CH3:27])=[CH:25][C:20]=4[N:19]=[CH:18]3)[CH:14]=[CH:15][CH:16]=2)=[CH:5][N:4]=1.C(OCC)(=O)C.C(=O)([O-])[O-].[Na+].[Na+]>Cl>[CH3:1][O:2][C:3]1[N:8]=[C:7]([O:9][CH3:10])[C:6]([C:11]2[CH:12]=[C:13]([N:17]3[C:21]4[CH:22]=[CH:23][C:24]([CH:26]([NH2:28])[CH3:27])=[CH:25][C:20]=4[N:19]=[CH:18]3)[CH:14]=[CH:15][CH:16]=2)=[CH:5][N:4]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 11983416N-(1-{1-[3-(2,4-Dimethoxy-pyrimidin-5-yl)-phenyl]-1H-benzoimidazol-5-yl}-ethyl)-formamide

Product 1

HCID 119834171-{1-[3-(2,4-Dimethoxy-pyrimidin-5-yl)-phenyl]-1H-benzoimidazol-5-yl}-ethylamineYield 25%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of N-(1-{1-[3-(2,4-dimethoxy-pyrimidin-5-yl)-phenyl]-1H-benzoimidazol-5-yl}-ethyl)-formamide (0.53 g, 1.31 mmol) in hydrochloric acid (2.2 ml, 6M) was stirred at 60° C. for 3 hours. To the cooled solution was added ethyl acetate and aqueous sodium carbonate to basic reaction. The layers were separated and the organic layer was dried over magnesium sulphate and concentrated in vacuo. The concentrate was eluted through silica gel with a mixture of dichloromethane, methanol and aqueous ammonia (9:1:0.1 v/v/v) to afford the desired product (0.12 g, 25%). LC-ESI-HRMS of [M+H]+ shows 376.1794 Da. Calc. 376.17735 Da. dev. 5.4 ppm.

Workup

  1. customto basic reaction
  2. customThe layers were separated
  3. dry with materialthe organic layer was dried over magnesium sulphate
  4. concentrationconcentrated in vacuo
  5. washThe concentrate was eluted through silica gel with a mixture of dichloromethane, methanol and aqueous ammonia (9:1:0.1 v/v/v)

Sources & evidence

ORD record
ord-0eac32c6e79d40a5bcdcf185e8d1ebbb
Source dataset
uspto-grants-2010_12
Patent number
US07851490B2

Reaction notes

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