2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → Ethyl 5-amino-2-methylthio-4-(3-methoxyphenyl)-quinazoline-6-carboxylate
Reaction equation
[NH2:1][C:2]1[C:3]2[C:4]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH3:26])[CH:20]=3)=[N:5][C:6]([S:17][CH3:18])=[N:7][C:8]=2[CH2:9][CH2:10][C:11]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>C(Cl)Cl>[NH2:1][C:2]1[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH3:26])[CH:20]=1)=[N:5][C:6]([S:17][CH3:18])=[N:7]2Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Ethyl 5-amino-2-methylthio-4-(3-methoxyphenyl)-7,8-dihydroquinazoline-6-carboxylate (example 25c, 22 mg) was dissolved in CH2Cl2 (1 ml). A 0.06M solution of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone in CH2Cl2 (1.2 ml) was added and the mixture was stirred at room temperature for 15 min. The reaction mixture was concentrated under reduced pressure. The title compound was purified by chromatography on silica gel with toluene/EtOAc=95/5 (v/v) as eluent.