3-bromo-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one → HCID 67547673, compound

HRID 1801681Notes

Reaction equation

HRID 1801681 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].[CH:14]1([CH2:17][O:18][C:19]2[C:26]([O:27][CH3:28])=[CH:25][CH:24]=[CH:23][C:20]=2[CH:21]=O)[CH2:16][CH2:15]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:21]/[C:20]1[CH:23]=[CH:24][CH:25]=[C:26]([O:27][CH3:28])[C:19]=1[O:18][CH2:17][CH:14]1[CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 2915243-bromo-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-oneHCID 2723922Sodium ethoxideHCID 435604072-(Cyclopropylmethoxy)-3-methoxybenzaldehyde

Product 1

HCID 67547673HCID 67547673, 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 (1.0 g, 4.181 mmol) and 2-(cyclopropylmethoxy)-3-methoxybenzaldehyde (1.29 g, 6.255 mmol) in the presence of sodium ethoxide (0.56 g, 8.361 mmol) in absolute ethanol (30 ml) as described in Intermediate 1 to give 424 mg of the product as a light yellow solid; 1H NMR (300 MHz, CDCl3) δ 0.35-0.40 (m, 2H), 0.60-0.79 (m, 2H), 1.30-1.40 (m, 1H), 3.82-3.90 (m, 5H), 6.90 (d, J=7.8 Hz, 1H), 7.04-7.12 (m, 2H), 7.33 (d, J=7.8 Hz, 1H), 7.62-7.72 (m, 3H), 8.48 (d, J=15.6 Hz, 1H), 8.95 (d, J=7.5 Hz, 1H).

Sources & evidence

ORD record
ord-56bc510937724e718e2d80ca57835263
Source dataset
uspto-grants-2013_01
Patent number
US08349846B2

Reaction notes

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