Ammonia → 2-((2-Amino-5-nitropyrimidin-4-yl)amino)ethan-1-ol

HRID 273275Notes

Reaction equation

HRID 273275 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH2:10][OH:11])[C:5]([N+:12]([O-:14])=[O:13])=[CH:4][N:3]=1.[NH3:15]>>[NH2:15][C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH2:10][OH:11])[C:5]([N+:12]([O-:14])=[O:13])=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 116801462-((2-Chloro-5-nitropyrimidin-4-yl)amino)ethan-1-ol

Product 1

HCID 115139392-((2-Amino-5-nitropyrimidin-4-yl)amino)ethan-1-olYield 93%

Conditions

Temperature
55 °C

Procedure

21.86 g (0.1 mole) of 2-chloro-4-(2-hydroxyethylamino)-5-nitropyrimidine was dissolved in 500 ml of ammonia saturated ethanol solution, and maintained between 50-60° C. A stream of ammonia was bubbled through the mixture for 13 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 18.81 g (93% yield) of light yellow-colored 2-amino-4-(2-hydroxyethylamino)-5-nitropyrimidine.

Workup

  1. customA stream of ammonia was bubbled through the mixture for 13 hours
  2. customAfter completion of the reaction
  3. temperaturethe reaction product was maintained below 5° C.
  4. filtrationthe resulting crystal was filtered
  5. washwashed
  6. customdried

Sources & evidence

ORD record
ord-df7ca7db069b449ea4e465f9d3607e1a
Source dataset
uspto-grants-2008_11
Patent number
US07456282B2

Reaction notes

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