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

HRID 1801679Notes

Reaction equation

HRID 1801679 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][CH2:29][CH3:30])=[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][CH2:29][CH3:30]

Participants

5

Reactant 3

HCID 2915243-bromo-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-oneHCID 2723922Sodium ethoxideHCID 20985816HCID 20985816, compound

Product 1

HCID 675477013-Bromo-2-{(E)-2-[2-(hexyloxy)-3-methoxyphenyl]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 (1.501 g, 6.271 mmol) and 3-methoxy-2-(hexyloxy)benzaldehyde (1.642 g, 6.942 mmol) in the presence of sodium ethoxide (0.642 g, 9.401 mmol) in absolute ethanol (30 ml) as described in Intermediate 1 to give 986 mg of the product as a light yellow solid; 1H NMR (300 MHz, CDCl3) δ 0.84-0.90 (m, 3H), 1.30-1.38 (m, 4H), 1.52-1.58 (m, 2H), 1.88 (t, J=6.9 Hz, 2H) 3.87 (s, 3H), 4.01 (t, J=6.9 Hz, 2H), 6.90 (d, J=8.1 Hz, 1H), 7.04-7.10 (m, 2H), 7.31 (d, J=7.8 Hz, 1H), 7.59-7.70 (m, 3H), 8.38 (d, J=15.6 Hz, 1H), 8.94 (d, J=7.5 Hz, 1H).

Sources & evidence

ORD record
ord-343a0611958d42e39f8481e984155ae0
Source dataset
uspto-grants-2013_01
Patent number
US08349846B2

Reaction notes

Loading…