Potassium Iodide → 4-(3-Acetoxy-4-methylanilino)-6-methoxy-7-(3-thienylmethoxy)quinazoline

HRID 279506Notes

Reaction equation

HRID 279506 reaction equation
Cl.[C:2]([O:5][C:6]1[CH:7]=[C:8]([CH:23]=[CH:24][C:25]=1[CH3:26])[NH:9][C:10]1[C:19]2[C:14](=[CH:15][C:16]([OH:22])=[C:17]([O:20][CH3:21])[CH:18]=2)[N:13]=[CH:12][N:11]=1)(=[O:4])[CH3:3].[I-].[K+].Cl[CH2:30][C:31]1[CH:35]=[CH:34][S:33][CH:32]=1>>[C:2]([O:5][C:6]1[CH:7]=[C:8]([CH:23]=[CH:24][C:25]=1[CH3:26])[NH:9][C:10]1[C:19]2[C:14](=[CH:15][C:16]([O:22][CH2:30][C:31]3[CH:35]=[CH:34][S:33][CH:32]=3)=[C:17]([O:20][CH3:21])[CH:18]=2)[N:13]=[CH:12][N:11]=1)(=[O:4])[CH3:3]

Participants

4

Reactant 3

HCID 4875Potassium IodideHCID 124874623-(Chloromethyl)thiopheneHCID 1356711804-(3-Acetoxy-4-methylanilino)-7-hydroxy-6-methoxyquinazoline hydrochloride

Product 1

HCID 226249964-(3-Acetoxy-4-methylanilino)-6-methoxy-7-(3-thienylmethoxy)quinazolineYield 46%

Procedure

Using an analogous procedure to that described for the starting material in Example 1, 4-(3-acetoxy-4-methylanilino)-7-hydroxy-6-methoxyquinazoline hydrochloride (400 mg) was reacted in the presence of catalytic potassium iodide with 3-chloromethylthiophene (Journal of the Chemical Society 1958, 4202) (168 mg) to give 4-(3-acetoxy-4-methylanilino)-6-methoxy-7-(3-thienylmethoxy)quinazoline (210 mg, 46%).

Sources & evidence

ORD record
ord-bea83190cab9425fac1ad8e961591c7a
Source dataset
uspto-grants-2002_03
Patent number
US06362336B1

Reaction notes

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