1,3-Benzodioxole-4-carboxaldehyde → 2-[(E)-2-(1,3-Benzodioxol-4-yl)vinyl]-3-bromo-4H-pyrido[1,2-a]pyrimidin-4-one

HRID 1801675Notes

Reaction equation

HRID 1801675 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].[O:14]1[C:18]2[CH:19]=[CH:20][CH:21]=[C:22]([CH:23]=O)[C:17]=2[O:16][CH2:15]1.[O-]CC.[Na+]>C(O)C>[O:14]1[C:18]2[CH:19]=[CH:20][CH:21]=[C:22](/[CH:23]=[CH:13]/[C:3]3[N:4]=[C:5]4[CH:12]=[CH:11][CH:10]=[CH:9][N:6]4[C:7](=[O:8])[C:2]=3[Br:1])[C:17]=2[O:16][CH2:15]1

Participants

5

Reactant 3

HCID 822641,3-Benzodioxole-4-carboxaldehydeHCID 2915243-bromo-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-oneHCID 2723922Sodium ethoxide

Product 1

HCID 675483572-[(E)-2-(1,3-Benzodioxol-4-yl)vinyl]-3-bromo-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 (1.5 g, 6.271 mmol) and 1,3-benzodioxole-4-carbaldehyde (1.12 g, 7.463 mmol) in the presence of sodium ethoxide (640 mg, 9.401 mmol) in absolute ethanol (100 ml) as described in Intermediate 1 to give 1.5 g of the product as a light yellow solid; 1H NMR (300 MHz, CDCl3) δ 4.48 (s, 2H), 6.83-6.89 (m, 2H), 7.05-7.10 (m, 2H), 7.19 (t, J=6.9 Hz, 1H), 7.69 (d, J=9.3 Hz, 1H), 7.78-7.85 (m, 1H), 7.97 (d, J=15.6 Hz, 1H), 8.94 (d, J=7.2 Hz, 1H).

Sources & evidence

ORD record
ord-6bdf3172791a46ff9afbd59d2f960306
Source dataset
uspto-grants-2013_01
Patent number
US08349846B2

Reaction notes

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