3,5-Di-tert-butyl-4-hydroxybenzaldehyde → 2-(3,5-di-tert-butyl-4-hydroxyphenyl)-5,7-dimethoxyquinazolin-4(3H)-one

HRID 336674Notes

Reaction equation

HRID 336674 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[C:7]([O:13][CH3:14])[C:3]=1[C:4]([NH2:6])=[O:5].[C:15]([C:19]1[CH:20]=[C:21]([CH:24]=[C:25]([C:28]([CH3:31])([CH3:30])[CH3:29])[C:26]=1[OH:27])[CH:22]=O)([CH3:18])([CH3:17])[CH3:16].COC1C=C(OC)C=C2C=1C(=O)NC(C1C=CC=CN=1)=N2>>[C:28]([C:25]1[CH:24]=[C:21]([C:22]2[NH:6][C:4](=[O:5])[C:3]3[C:2](=[CH:10][C:9]([O:11][CH3:12])=[CH:8][C:7]=3[O:13][CH3:14])[N:1]=2)[CH:20]=[C:19]([C:15]([CH3:18])([CH3:17])[CH3:16])[C:26]=1[OH:27])([CH3:31])([CH3:30])[CH3:29]

Participants

4

Reactant 3

HCID 732193,5-Di-tert-butyl-4-hydroxybenzaldehydeHCID 203490162-Amino-4,6-dimethoxybenzamideHCID 1360379985,7-dimethoxy-2-(pyridin-2-yl)quinazolin-4(3H)-one

Product 1

HCID 1360379912-(3,5-di-tert-butyl-4-hydroxyphenyl)-5,7-dimethoxyquinazolin-4(3H)-oneYield 41%

Procedure

2-(3,5-di-tert-butyl-4-hydroxyphenyl)-5,7-dimethoxyquinazolin-4(3H)-one was synthesized from 2-amino-4,6-dimethoxybenzamide and 3,5-di-tert-butyl-4-hydroxybenzaldehyde, using the method described for 5,7-dimethoxy-2-(pyridin-2-yl)quinazolin-4(3H)-one. 2-(3,5-di-tert-butyl-4-hydroxyphenyl)-5,7-dimethoxyquinazolin-4(3H)-one (130 mg, 41%) was isolated as a light yellow solid. Selected data: MS (m/z): 411.17; MP 229.7-230.5° C.

Sources & evidence

ORD record
ord-11c4cec7bdab4311a109014d6d0d34cb
Source dataset
uspto-grants-2014_11
Patent number
US08889698B2

Reaction notes

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