Nitric Acid → 2,4-Diamino-5-(3-amino-4-chloro-5-nitrophenyl)-6-ethylpyrimidine

HRID 1081651Notes

Reaction equation

HRID 1081651 reaction equation
[N+:1]([O-:4])(O)=[O:2].S(=O)(=O)(O)O.[NH2:10][C:11]1[N:16]=[C:15]([NH2:17])[C:14]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)=[C:13]([CH2:25][CH3:26])[N:12]=1.[OH-].[NH4+]>>[NH2:10][C:11]1[N:16]=[C:15]([NH2:17])[C:14]([C:18]2[CH:19]=[CH:20][C:21]([Cl:24])=[C:22]([N+:1]([O-:4])=[O:2])[CH:23]=2)=[C:13]([CH2:25][CH3:26])[N:12]=1

Participants

5

Reactant 4

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 4993PyrimethamineHCID 14923Ammonium Hydroxide

Product 1

HCID 3274042,4-Diamino-5-(3-amino-4-chloro-5-nitrophenyl)-6-ethylpyrimidine

Conditions

Temperature
50 °C

Procedure

A stirred solution of 75 mL of 70% nitric acid and 75 mL of concentrated sulfuric acid warmed to about 50° C. from the heat of solution. To this was added 25 grams (0.10 mole) of 2,4-diamino-5-(4-chloro-phenyl)-6-ethylpyrimidine (commercially available) during a 10 minute period. Upon completion of addition, the reaction mixture was stirred at 50° C. for about 1 hour. After this time, the reaction mixture was allowed to cool to ambient temperature where it was stirred for about 18 hours. The reaction mixture was then poured into 1000 mL of ice containing 110 mL of concentrated ammonium hydroxide. The resultant solid was collected by filtration and recrystallized from aqueous ethanol, yielding 29.2 grams of 2,4-diamino-5-(4-chloro-3-nitrophenyl)-6-ethylpyrimidine. The NMR spectrum was consistent with the proposed structure.

Workup

  1. temperatureheat of solution
  2. additionUpon completion of addition
  3. temperatureto cool to ambient temperature where it
  4. stirringwas stirred for about 18 hours
  5. filtrationThe resultant solid was collected by filtration
  6. customrecrystallized from aqueous ethanol

Sources & evidence

ORD record
ord-4cb071b01d024d94bccdb96f20c535d2
Source dataset
uspto-grants-1996_12
Patent number
US05587379

Reaction notes

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