3,4,5-Trimethoxybenzaldehyde → 3,9-Dimethyl-2-[trans-2-(3,4,5-trimethoxyphenyl)ethenyl]-4H-pyrido[1,2-a]pyrimidin-4-one

HRID 1580938Notes

Reaction equation

HRID 1580938 reaction equation
C[O-].[Na+].[CH3:4][C:5]1[N:6]=[C:7]2[C:16]([CH3:17])=[CH:15][CH:14]=[CH:13][N:8]2[C:9](=[O:12])[C:10]=1[CH3:11].[CH3:18][O:19][C:20]1[CH:21]=[C:22]([CH:25]=[C:26]([O:30][CH3:31])[C:27]=1[O:28][CH3:29])[CH:23]=O>C(O)C>[CH3:11][C:10]1[C:9](=[O:12])[N:8]2[CH:13]=[CH:14][CH:15]=[C:16]([CH3:17])[C:7]2=[N:6][C:5]=1/[CH:4]=[CH:23]/[C:22]1[CH:25]=[C:26]([O:30][CH3:31])[C:27]([O:28][CH3:29])=[C:20]([O:19][CH3:18])[CH:21]=1

Participants

5

Reactant 3

HCID 68583,4,5-TrimethoxybenzaldehydeHCID 10942334Sodium MethoxideHCID 123397192,3,9-Trimethyl-4H-pyrido[1,2-a]pyrimidin-4-one

Product 1

HCID 218537923,9-Dimethyl-2-[trans-2-(3,4,5-trimethoxyphenyl)ethenyl]-4H-pyrido[1,2-a]pyrimidin-4-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1.3g of sodium methoxide in 75ml of absolute ethanol is added 2.0g of 2,3,9-trimethyl-4H-pyrido-[1,2-a]pyrimidin-4-one, followed by 4.0g of 3,4,5-trimethoxybenzaldehyde. The mixture is stirred and heated under reflux for 89 hours. The reaction mixture is cooled, the solid is filtered, washed with 20ml of ether and 25ml of water, dried, and recrystallized from 75ml of acetonitrile to yield the title compound, melting point 218°-219°C dec.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 89 hours
  3. temperatureThe reaction mixture is cooled
  4. filtrationthe solid is filtered
  5. washwashed with 20ml of ether and 25ml of water
  6. customdried
  7. customrecrystallized from 75ml of acetonitrile

Sources & evidence

ORD record
ord-d89cf70173b24f458c8421a5b15a938f
Source dataset
uspto-grants-1976_01
Patent number
US03935197

Reaction notes

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