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

HRID 467738Notes

Reaction equation

HRID 467738 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:11]([Br:12])=[CH:10][N:9]=[C:8](S(C)(=O)=O)[N:7]=1)=[O:5])[CH3:2].[CH3:17][O:18][CH2:19][CH2:20][NH2:21]>ClCCl>[CH2:1]([O:3][C:4]([C:6]1[C:11]([Br:12])=[CH:10][N:9]=[C:8]([NH:21][CH2:20][CH2:19][O:18][CH3:17])[N:7]=1)=[O:5])[CH3:2]

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-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
45 °C

Procedure

A solution of 5-bromo-2-methanesulfonyl-pyrimidine-4-carboxylic acid ethyl ester (86 mg, 0.27 mmol) in dichloromethane (2 ml) was treated with 2-methoxyethylamine (124 μl, 1.44 mmol) under argon atmosphere and heated to 45° C. for 2 h. All volatiles were removed and the product was obtained after purification by silica gel chromatography using a heptane/ethyl acetate gradient as colorless oil (72 mg, 82%).

Workup

  1. customAll volatiles were removed
  2. customthe product was obtained
  3. customafter purification by silica gel chromatography

Sources & evidence

ORD record
ord-b0ffabf93b3540b7b562b86c74e247f1
Source dataset
uspto-grants-2014_01
Patent number
US08623866B2

Reaction notes

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