Ammonia → 2-Chloroquinazolin-4-amine
Reaction equation
[Cl:1][C:2]1[N:11]=[C:10](Cl)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[NH3:13]>C1COCC1.CCOC(C)=O>[Cl:1][C:2]1[N:11]=[C:10]([NH2:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of 2,4-dichloroquinazoline (2.0 g, 10 mmol) in THF (10 mL), was added ammonia (28-30% in water, 18 mL). The reaction mixture was stirred at room temperature overnight. The reaction mixture was diluted with EtOAc, washed with saturated NaHCO3, water and brine, dried over Na2SO4, filtered and evaporated. The resulting solid was washed with EtOAc to give the title compound (1.3 g, 72%). 1H NMR (400 MHz, DMSO-d6) δ7.52-7.48 (m, 1H), 7.6-7.58 (m, 1H), 7.8-7.76 (m, 1H), 8.22-8.20 (m, 1H), 8.32 (bs, 2H).
Workup
- washwashed with saturated NaHCO3, water and brine
- dry with materialdried over Na2SO4
- filtrationfiltered
- customevaporated
- washThe resulting solid was washed with EtOAc
Sources & evidence
- ORD record
- ord-0a687d3bfdb04c43b9ca57ac7844f968
- Source dataset
- uspto-grants-2013_09
- Patent number
- US08541421B2
Reaction notes
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