2-Methoxyethylamine → 1-(2-aminopyrimidin-4-yl)-6-bromo-N-(2-methoxyethyl)-1H-1,3-benzodiazol-2-amine

HRID 1398673Notes

Reaction equation

HRID 1398673 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[C:8](C(Cl)(Cl)Cl)[N:7]([C:14]3[CH:19]=[CH:18][N:17]=[C:16]([NH2:20])[N:15]=3)[C:6]=2[CH:21]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:28][O:29][CH2:30][CH2:31][NH2:32]>>[NH2:20][C:16]1[N:15]=[C:14]([N:7]2[C:6]3[CH:21]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]=3[N:9]=[C:8]2[NH:32][CH2:31][CH2:30][O:29][CH3:28])[CH:19]=[CH:18][N:17]=1

Participants

4

Reactant 3

HCID 80182-MethoxyethylamineHCID 10796Cesium carbonateHCID 681818334-[6-Bromo-2-(trichloromethyl)-1,3-benzodiazol-1-yl]pyrimidin-2-amine

Product 1

HCID 681817331-(2-aminopyrimidin-4-yl)-6-bromo-N-(2-methoxyethyl)-1H-1,3-benzodiazol-2-amineYield 39%

Procedure

A mixture of 4-[6-bromo-2-(trichloromethyl)-1H-1,3-benzodiazol-1-yl]pyrimidin-2-amine (1.5 g, 3.68 mmol) and cesium carbonate (2.5 g, 7.67 mmol) in 2-methoxyethan-1-amine (15 mL) was stirred under nitrogen for 3 days at room temperature. The reaction mixture was concentrated under vacuum and the residue was purified on a C18 column (acetonitrile/water, 5:95-80:20) to give 0.55 g (39%) of 1-(2-aminopyrimidin-4-yl)-6-bromo-N-(2-methoxyethyl)-1H-1,3-benzodiazol-2-amine as a yellow solid. LC-MS: m/z=+363 (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. customthe residue was purified on a C18 column (acetonitrile/water, 5:95-80:20)

Sources & evidence

ORD record
ord-c66b0c08f1964160b6e3a132f6f8eb3d
Source dataset
uspto-grants-2014_12
Patent number
US08901313B2

Reaction notes

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