Ethanol → HCID 67547229, compound

HRID 1801677Notes

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].COC[CH:17]([O:19][C:20]1[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=1[CH:22]=O)[CH3:18].[O-:28][CH2:29]C.[Na+].[CH2:32](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:22]/[C:21]1[CH:24]=[CH:25][CH:26]=[C:27]([O:28][CH3:29])[C:20]=1[O:19][CH2:17][CH2:18][CH3:32]

Participants

Reactant 4

HCID 702Ethanol

HCID 2915243-bromo-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one

HCID 2723922Sodium ethoxide

HCID 64122985HCID 64122985, compound

Product 1

HCID 67547229HCID 67547229, compound

Procedure

The title compound was prepared from 3-bromo-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one (1.2 g, 5.012 mmol) and (3-methoxy-2-propoxy)benzaldehyde (1.17 g, 6.021 mmol) in the presence of sodium ethoxide (0.512 g, 7.521 mmol) in absolute ethanol (25 ml) as described in Intermediate 1 to give 681 mg of the product as a light yellow solid; 1H NMR (300 MHz, CDCl3) δ 1.15 (t, J=7.8 Hz, 3H), 1.89 (q, J=7.2 Hz, 2H), 3.87 (s, 3H), 3.99 (t, J=6.6 Hz, 2H), 6.91 (d, J=7.5 Hz, 1H), 7.05-7.11 (m, 2H), 7.33 (d, J=7.2 Hz, 1H), 7.58-7.70 (m, 3H), 8.42 (d, J=13.8 Hz, 1H), 8.94 (d, J=6.9 Hz, 1H).

Sources & evidence

ORD record: ord-1dbb4f6545624b23bdda115ee598c1b7
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08349846B2

Reaction notes

Loading…