3-bromo-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one → HCID 67547984, compound

HRID 1801680Notes

Reaction equation

HRID 1801680 reaction equation
[Br:1][C:2]1[C:7](=[O:8])[N:6]2[CH:9]=[CH:10][CH:11]=[CH:12][C:5]2=[N:4][C:3]=1[CH3:13].[CH3:14][N:15]([CH3:29])[CH2:16][CH2:17][O:18][C:19]1[C:26]([O:27][CH3:28])=[CH:25][CH:24]=[CH:23][C:20]=1[CH:21]=O.[O-]CC.[Na+]>C(O)C>[Br:1][C:2]1[C:7](=[O:8])[N:6]2[CH:9]=[CH:10][CH:11]=[CH:12][C:5]2=[N:4][C:3]=1/[CH:13]=[CH:21]/[C:20]1[CH:23]=[CH:24][CH:25]=[C:26]([O:27][CH3:28])[C:19]=1[O:18][CH2:17][CH2:16][N:15]([CH3:29])[CH3:14]

Participants

5

Reactant 3

HCID 2915243-bromo-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-oneHCID 2723922Sodium ethoxideHCID 65042432-[2-(dimethylamino)ethoxy]-3-methoxybenzaldehyde

Product 1

HCID 67547984HCID 67547984, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The title compound was prepared from 3-bromo-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one (1.021 g, 4.18 mmol) and 2-[2-(dimethylamino)ethoxy]-3-methoxybenzaldehyde (0.969 g, 5.011 mmol) in the presence of sodium ethoxide (0.426 g, 6.27 mmol) in absolute ethanol (25 ml) as described in Intermediate 1 to give 649 mg of the product as a light yellow solid; 1H NMR (300 MHz, CDCl3) δ 2.39 (s, 6H), 2.82 (s, 2H), 3.87 (s, 3H), 4.12 (s, 2H), 6.91 (d, J=7.5 Hz, 1H), 7.04-7.10 (m, 2H), 7.28-7.34 (m, 1H), 7.66-7.71 (m, 3H), 8.40 (d, J=15.0 Hz, 1H), 8.95 (d, J=7.2 Hz, 1H).

Sources & evidence

ORD record
ord-b6e4363460c841c19a5861dfd77dc57d
Source dataset
uspto-grants-2013_01
Patent number
US08349846B2

Reaction notes

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