Ethanolamine → 2-[(2-Amino-6-chloropyrimidin-4-yl)amino]ethan-1-ol

HRID 1421868Notes

Reaction equation

HRID 1421868 reaction equation
[OH:1][CH2:2][CH2:3][NH2:4].[NH2:5][C:6]1[N:11]=[C:10](Cl)[CH:9]=[C:8]([Cl:13])[N:7]=1.C(O)C>C(N(CC)CC)C>[NH2:5][C:6]1[N:11]=[C:10]([NH:4][CH2:3][CH2:2][OH:1])[CH:9]=[C:8]([Cl:13])[N:7]=1

Participants

5

Reactant 3

HCID 700EthanolamineHCID 702EthanolHCID 655222-Amino-4,6-dichloropyrimidine

Product 1

HCID 2358982-[(2-Amino-6-chloropyrimidin-4-yl)amino]ethan-1-olYield 59.6%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To 2-hydroxyethylamine (2.6 g, 42.7 mmol) were added 2-amino-4,6-dichloropyrimidine (7.0 g, 42.7 mmol), ethanol (150 ml) and triethylamine (6.6 ml), and the mixture was refluxed for one day. The solvent was distilled away under reduced pressure and the residue was washed with water, which was followed by recrystallization from chloroform to give yellow prism crystals (4.8 g, 59.6%), m.p. 143-146° C. (chloroform).

Workup

  1. temperaturethe mixture was refluxed for one day
  2. distillationThe solvent was distilled away under reduced pressure
  3. washthe residue was washed with water, which
  4. customwas followed by recrystallization from chloroform

Sources & evidence

ORD record
ord-17e0194cc5d94148954e504f51211d7c
Source dataset
uspto-grants-2000_06
Patent number
US06080750

Reaction notes

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