2-Methoxyethylamine → Ethyl 5-bromo-2-((2-methoxyethyl)amino)pyrimidine-4-carboxylate

HRID 1260309Notes

Reaction equation

HRID 1260309 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][NH2:5].[CH2:6]([O:8][C:9]([C:11]1[C:16]([Br:17])=[CH:15][N:14]=[C:13](S(C)(=O)=O)[N:12]=1)=[O:10])[CH3:7]>ClCCl>[CH2:6]([O:8][C:9]([C:11]1[C:16]([Br:17])=[CH:15][N:14]=[C:13]([NH:5][CH2:4][CH2:3][O:2][CH3:1])[N:12]=1)=[O:10])[CH3:7]

Participants

4

Reactant 2

HCID 80182-MethoxyethylamineHCID 67299941Ethyl 5-bromo-2-(methylsulfonyl)pyrimidine-4-carboxylate

Product 1

HCID 58368043Ethyl 5-bromo-2-((2-methoxyethyl)amino)pyrimidine-4-carboxylateYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Methoxyethylamine (0.278 ml, 3.2 mmol) was added at room temperature to a solution of 5-bromo-2-methanesulfonyl-pyrimidine-4-carboxylic acid ethyl ester (0.2 g, 0.65 mmol) in dichloromethane (5 ml). Stirring was continued at 45° C. for 2 hours. The solvent was evaporated and the crude product was purified by silica gel chromatography using an ethyl acetate/heptane eluent to yield the title compound as colorless oil (0.175 g, 89%).

Workup

  1. customThe solvent was evaporated
  2. customthe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-1abf7d8d65ab444e9d0f8e28ffc62ae5
Source dataset
uspto-grants-2013_06
Patent number
US08470820B2

Reaction notes

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