3-bromo-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one → 3-Bromo-2-{(E)-2-[3-methoxy-2-(pentyloxy)phenyl]vinyl}-4H-pyrido[1,2-a]pyrimidin-4-one

HRID 1801678Notes

Reaction equation

HRID 1801678 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][O:15][C:16]1[C:17]([O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])=[C:18]([CH:21]=[CH:22][CH:23]=1)[CH:19]=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:19]/[C:18]1[CH:21]=[CH:22][CH:23]=[C:16]([O:15][CH3:14])[C:17]=1[O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]

Participants

5

Reactant 3

HCID 2915243-bromo-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-oneHCID 2723922Sodium ethoxideHCID 193632903-Methoxy-2-(pentyloxy)benzaldehyde

Product 1

HCID 675484673-Bromo-2-{(E)-2-[3-methoxy-2-(pentyloxy)phenyl]vinyl}-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 (1.20 g, 5.01 mmol) and 3-methoxy-2-(pentyloxy)benzaldehyde (1.22 g, 5.521 mmol) in the presence of sodium ethoxide (0.512 g, 7.52 mmol) in absolute ethanol (30 ml) as described in Intermediate 1 to give 625 mg of the product as a light yellow solid; 1H NMR (300 MHz, CDCl3) δ 0.92 (t, J=6.9 Hz, 3H), 1.40 (q, J=7.2 Hz, 2H), 1.51-1.59 (m, 2H), 1.85 (q, J=7.8 Hz, 2H) 3.87 (s, 3H), 4.01 (t, J=6.3 Hz, 2H), 6.91 (d, J=7.8 Hz, 1H), 7.05-7.11 (m, 2H), 7.33 (d, J=7.8 Hz, 1H), 7.60-7.71 (m, 3H), 8.40 (d, J=15.9 Hz, 1H), 8.96 (d, J=6.6 Hz, 1H).

Sources & evidence

ORD record
ord-5558bd46d1214955ac55a99fef030fba
Source dataset
uspto-grants-2013_01
Patent number
US08349846B2

Reaction notes

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