2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → Ethyl 5-amino-2-methylthio-4-(3-methoxyphenyl)-quinazoline-6-carboxylate

HRID 1766083Notes

Reaction equation

HRID 1766083 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]2

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 21109093Ethyl 5-amino-2-methylthio-4-(3-methoxyphenyl)-7,8-dihydroquinazoline-6-carboxylate

Product 1

HCID 21109094Ethyl 5-amino-2-methylthio-4-(3-methoxyphenyl)-quinazoline-6-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

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.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customThe title compound was purified by chromatography on silica gel with toluene/EtOAc=95/5 (v/v) as eluent

Sources & evidence

ORD record
ord-40e0c5e489d0402c8ccbb17806d34391
Source dataset
uspto-grants-2007_06
Patent number
US07229990B2

Reaction notes

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