Hydrochloric Acid → 2,4-Diamino-5-[4-(3,3-diethyl-1-triazeno)-3,5-dimethoxy-benzyl]-pyrimidine
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:24]([O-])=O.[Na+].[CH2:28]([NH:30][CH2:31][CH3:32])[CH3:29]>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:24][N:30]([CH2:31][CH3:32])[CH2:28][CH3:29])=[C:16]([O:18][CH3:19])[CH:17]=2)=[CH:6][N:5]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
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 during 5 minutes with stirring and ice-cooling with a solution of 1.52 g. of sodium nitrite in 10 ml. of water. The solution was stirred at 0° C. for 30 minutes and 14.6 g. of diethylamine were then added. After stirring with ice-cooling for 2 hours, the precipitate was removed by filtration with suction, washed with water and recrystallized from methanol, whereby there was obtained 2,4-diamino-5-[4-(3,3-diethyl-1-triazeno)-3,5-dimethoxy-benzyl]-pyrimidine having a melting point of 196°-197° C. (decomposition).
Workup
- temperatureice-cooling with a solution of 1.52 g
- stirringThe solution was stirred at 0° C. for 30 minutes
- stirringAfter stirring with ice-
- temperaturecooling for 2 hours
- customthe precipitate was removed by filtration with suction
- washwashed with water
- customrecrystallized from methanol
Sources & evidence
- ORD record
- ord-754b973fca3141cc93e198cb7158f25a
- Source dataset
- uspto-grants-1987_04
- Patent number
- US04659818
Reaction notes
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