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

HRID 336673Notes

Reaction equation

HRID 336673 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][CH:18]=[C:17]([CH:21]=O)[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:17]1[CH:16]=[N:15][CH:20]=[CH:19][CH:18]=1)=[N:1]2

Participants

4

Reactant 3

HCID 103713-PyridinecarboxaldehydeHCID 203490162-Amino-4,6-dimethoxybenzamideHCID 1360379985,7-dimethoxy-2-(pyridin-2-yl)quinazolin-4(3H)-one

Product 1

HCID 1359078645,7-Dimethoxy-2-(pyridin-3-yl)quinazolin-4(3H)-oneYield 48%

Procedure

5,7-Dimethoxy-2-(pyridin-3-yl)quinazolin-4(3H)-one was synthesized from 2-amino-4,6-dimethoxybenzamide and 3-pyridine carboxaldehyde, using the method described for 5,7-dimethoxy-2-(pyridin-2-yl)quinazolin-4(3H)-one. 5,7-Dimethoxy-2-(pyridin-3-yl)quinazolin-4(3H)-one (105 mg, 48%) was isolated as a white solid. Selected data: MS (m/z): 284.0; MP 257-259° C. (hydrochloride).

Sources & evidence

ORD record
ord-b8e0bc7fd3f34ab2a2efa69e470c2272
Source dataset
uspto-grants-2014_11
Patent number
US08889698B2

Reaction notes

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