3-bromo-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one → HCID 67547242, compound

HRID 1801682Notes

Reaction equation

HRID 1801682 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([O:19][C:20]2[C:27]([O:28][CH3:29])=[CH:26][CH:25]=[CH:24][C:21]=2[CH:22]=O)[CH2:18][CH2:17][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:22]/[C:21]1[CH:24]=[CH:25][CH:26]=[C:27]([O:28][CH3:29])[C:20]=1[O:19][CH:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 2915243-bromo-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-oneHCID 2723922Sodium ethoxideHCID 6484666HCID 6484666, compound

Product 1

HCID 67547242HCID 67547242, 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 (700 mg, 2.921 mmol) and 2-(cyclopentyloxy)-3-methoxybenzaldehyde (998 mg, 4.391 mmol) in the presence of sodium ethoxide (398 mg, 5.842 mmol) in absolute ethanol (30 ml) as described in Intermediate 1 to give 358 mg of the product as a light yellow solid; IR (KBr) 2958, 1679, 1620, 1528, 1436, 1264, 1065, 971 cm−1; 1H NMR (300 MHz, CDCl3) δ 1.60-1.75 (m, 4H), 1.95-2.10 (m, 4H), 3.87 (s, 3H), 4.94 (br s, 1H), 6.90 (d, J=7.8 Hz, 1H), 7.02-7.10 (m, 1H), 7.35 (d, J=7.5 Hz, 2H), 7.56-7.72 (m, 3H), 8.44 (d, J=16.2 Hz, 1H), 8.94 (d, J=7.2 Hz, 1H).

Sources & evidence

ORD record
ord-46f7e18b784644f49cb59e55fcfa1fe3
Source dataset
uspto-grants-2013_01
Patent number
US08349846B2

Reaction notes

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