Ethanolamine → 2-((2-Chloro-5-nitropyrimidin-4-yl)amino)ethan-1-ol

HRID 273274Notes

Reaction equation

HRID 273274 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1.[CH2:12]([CH2:14][NH2:15])[OH:13]>C(O)C.CO>[Cl:1][C:2]1[N:7]=[C:6]([NH:15][CH2:14][CH2:12][OH:13])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1

Participants

5

Reactant 2

HCID 700EthanolamineHCID 5212662,4-Dichloro-5-nitropyrimidine

Product 1

HCID 116801462-((2-Chloro-5-nitropyrimidin-4-yl)amino)ethan-1-olYield 81%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

19.40 g (0.1 mole) of 2,4-dichloro-5-nitropyrimidine was completely dissolved in 60 ml of ethanol and maintained below 15° C. To this solution, a solution of 12.22 g (0.2 mole) of ethanolamine in 20 ml of methanol was added slowly while maintaining the temperature of a reactor below 20° C. The mixture was stirred below 15° C. for 18 hours. After completion of the reaction, the reaction product was maintained below 5° C., and the resulting crystal was filtered, washed and dried, thereby giving 17.71 g (81% yield) of light yellow-colored 2-chloro-4-(2-hydroxyethylamino)-5-nitropyrimidine.

Workup

  1. temperaturemaintained below 15° C
  2. temperaturewhile maintaining the temperature of a reactor below 20° C
  3. customAfter completion of the reaction
  4. temperaturethe reaction product was maintained below 5° C.
  5. filtrationthe resulting crystal was filtered
  6. washwashed
  7. customdried

Sources & evidence

ORD record
ord-ebe8d67107094edb81775b54ea88a9ed
Source dataset
uspto-grants-2008_11
Patent number
US07456282B2

Reaction notes

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