4-Pyridinecarboxaldehyde → 5,7-Dimethoxy-2-(pyridin-4-yl)quinazolin-4(3H)-one

HRID 336679Notes

Reaction equation

HRID 336679 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].[N:15]1[CH:20]=[CH:19][C:18]([CH:21]=O)=[CH:17][CH:16]=1.COC1C=C(OC)C=C2C=1C(=O)NC(C1C=CC=CN=1)=N2>>[CH3:14][O:13][C:7]1[CH:8]=[C:9]([O:11][CH3:12])[CH:10]=[C:2]2[C:3]=1[C:4](=[O:5])[NH:6][C:21]([C:18]1[CH:19]=[CH:20][N:15]=[CH:16][CH:17]=1)=[N:1]2

Participants

4

Reactant 3

HCID 133894-PyridinecarboxaldehydeHCID 203490162-Amino-4,6-dimethoxybenzamideHCID 1360379985,7-dimethoxy-2-(pyridin-2-yl)quinazolin-4(3H)-one

Product 1

HCID 1360379625,7-Dimethoxy-2-(pyridin-4-yl)quinazolin-4(3H)-oneYield 63%

Procedure

5,7-Dimethoxy-2-(pyridin-4-yl)quinazolin-4(3H)-one was synthesized from 2-amino-4,6-dimethoxybenzamide and 4-pyridine carboxaldehyde, using the method described for 5,7-dimethoxy-2-(pyridin-2-yl)quinazolin-4(3H)-one. 5,7-Dimethoxy-2-(pyridin-4-yl)quinazolin-4(3H)-one (142 mg, 63%) was isolated as a pale brown solid and then converted to the corresponding hydrochloride (yellow solid). Selected data: MS (m/z): 284.06; MP 294-295° C. (hydrochloride).

Sources & evidence

ORD record
ord-6bb2fdc6592f4424972eaa035f488988
Source dataset
uspto-grants-2014_11
Patent number
US08889698B2

Reaction notes

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