3-Pyridinecarboxaldehyde → 3-Bromo-2-[(E)-2-pyridin-3-ylvinyl]-4H-pyrido[1,2-a]pyrimidin-4-one

HRID 1801673Notes

Reaction equation

HRID 1801673 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].[N:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH:20]=O)[CH:15]=1.[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:20]/[C:16]1[CH:15]=[N:14][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 103713-PyridinecarboxaldehydeHCID 2915243-bromo-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-oneHCID 2723922Sodium ethoxide

Product 1

HCID 675476553-Bromo-2-[(E)-2-pyridin-3-ylvinyl]-4H-pyrido[1,2-a]pyrimidin-4-one

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 (250 mg, 1.045 mmol) and pyridine-3-aldehyde (168 mg, 1.561 mmol) in the presence of sodium ethoxide (142 mg, 2.086 mmol) in absolute ethanol (25 ml) as described in Intermediate 1 to give 203 mg of the product as a light yellow solid; 1H NMR (300 MHz, CDCl3) δ 7.11 (t, J=6.9 Hz, 1H), 7.32-7.36 (m, 1H), 7.63-7.76 (m, 3H), 7.98-8.05 (m, 2H), 8.57 (d, J=4.8 Hz, 1H), 8.35 (s, 1H), 8.97 (d, J=6.6 Hz, 1H).

Sources & evidence

ORD record
ord-f69a164183424a46a6ec074ccc3cf2f6
Source dataset
uspto-grants-2013_01
Patent number
US08349846B2

Reaction notes

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