Ammonia → 4-Allylamino-2-amino-6-nitroquinazoline
Reaction equation
[NH3:1].[CH2:2]([NH:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([N+:16]([O-:18])=[O:17])[CH:14]=2)[N:9]=[C:8](Cl)[N:7]=1)[CH:3]=[CH2:4].O>C(O)C.C1COCC1>[CH2:2]([NH:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([N+:16]([O-:18])=[O:17])[CH:14]=2)[N:9]=[C:8]([NH2:1])[N:7]=1)[CH:3]=[CH2:4]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 70 °C
Procedure
After 10 ml of ammonia gas was dissolved in 50 ml of ethanol at −78° C., 15 ml of a solution of 2.40 g (9.07 mmol) of 4-allylamino-2-chloro-6-nitroquinazoline in THF was added thereto, followed by stirring overnight in a sealed tube at 70° C. 150 ml of water was added to the reaction solution, and then crystals thus precipitated were filtered out, followed by recrystallization from ethyl acetate-hexane to give 1.88 g (84.6%) of the title compound.
Workup
- customcrystals thus precipitated
- filtrationwere filtered out
- customfollowed by recrystallization from ethyl acetate-hexane
Sources & evidence
- ORD record
- ord-7c7ed0f66cac43b9ae8d0ea76fa0da79
- Source dataset
- uspto-grants-2002_01
- Patent number
- US06339089B2
Reaction notes
Loading…