Hydrochloric Acid → 2,4-Diamino-5-(4-azido-3,5-dimethoxy-benzyl)pyrimidine

HRID 542964Notes

Reaction equation

HRID 542964 reaction equation
Cl.Cl.[NH2:3][C:4]1[N:9]=[C:8]([NH2:10])[C:7]([CH2:11][C:12]2[CH:17]=[C:16]([O:18][CH3:19])[C:15]([NH2:20])=[C:14]([O:21][CH3:22])[CH:13]=2)=[CH:6][N:5]=1.Cl.N([O-])=O.[Na+].[N-:28]=[N+:29]=[N-].[Na+].C(=O)(O)[O-].[Na+]>O>[NH2:3][C:4]1[N:9]=[C:8]([NH2:10])[C:7]([CH2:11][C:12]2[CH:13]=[C:14]([O:21][CH3:22])[C:15]([N:20]=[N+:28]=[N-:29])=[C:16]([O:18][CH3:19])[CH:17]=2)=[CH:6][N:5]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 33557Sodium AzideHCID 516892Sodium BicarbonateHCID 212809862,4-Diamino-5-(4-amino-3,5-dimethoxy-benzyl)pyrimidine dihydrochlorideHCID 23668193Sodium Nitrite

Product 1

HCID 212809452,4-Diamino-5-(4-azido-3,5-dimethoxy-benzyl)pyrimidine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

A solution of 7 g. of 2,4-diamino-5-(4-amino-3,5-dimethoxy-benzyl)-pyrimidine dihydrochloride in 60 ml. of 1N hydrochloric acid and 40 ml. of water was treated over a period of 5 minutes with stirring and ice-cooling with a solution of 1.52 g. of sodium nitrite in 10 ml. of water. After stirring at 0° C. for 30 minutes, a solution of 1.43 g. of sodium azide in 20 ml. of water was added. The solution was stirred at 0° C. for 2 hours and then treated with sodium bicarbonate to obtain an alkaline reaction. After stirring at 0° C. for 1 hour, the precipitate was removed by filtration with suction, washed with water and recrystallized from methanol, whereby there was obtained 2,4-diamino-5-(4-azido-3,5-dimethoxy-benzyl)-pyrimidine having a melting point of 152° C. (decomposition).

Workup

  1. temperatureice-cooling with a solution of 1.52 g
  2. stirringAfter stirring at 0° C. for 30 minutes
  3. stirringThe solution was stirred at 0° C. for 2 hours
  4. customto obtain
  5. customan alkaline reaction
  6. stirringAfter stirring at 0° C. for 1 hour
  7. customthe precipitate was removed by filtration with suction
  8. washwashed with water
  9. customrecrystallized from methanol

Sources & evidence

ORD record
ord-8be0f7f08f52429fb7c3d546637b9f8f
Source dataset
uspto-grants-1987_04
Patent number
US04659818

Reaction notes

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