3,4,5-Trimethoxybenzaldehyde → HCID 56616028, compound

HRID 1580937Notes

Reaction equation

HRID 1580937 reaction equation
C[O-].[Na+].[CH3:4][C:5]1[N:6]=[C:7]2[C:15]([CH3:16])=[CH:14][CH:13]=[CH:12][N:8]2[C:9](=[O:11])[CH:10]=1.[CH3:17][O:18][C:19]1[CH:20]=[C:21]([CH:24]=[C:25]([O:29][CH3:30])[C:26]=1[O:27][CH3:28])[CH:22]=O>CO>[CH3:16][C:15]1[C:7]2=[N:6][C:5]([CH:4]=[CH:22][C:21]3[CH:24]=[C:25]([O:29][CH3:30])[C:26]([O:27][CH3:28])=[C:19]([O:18][CH3:17])[CH:20]=3)=[CH:10][C:9](=[O:11])[N:8]2[CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 68583,4,5-TrimethoxybenzaldehydeHCID 5239852,9-Dimethyl-4H-pyrido(1,2-a)pyrimidin-4-oneHCID 10942334Sodium Methoxide

Product 1

HCID 56616028HCID 56616028, compoundYield 21.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2.2g of sodium methoxide in 100ml of absolute methanol is added 3.5g of 2,9-dimethyl-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 28 hours. A crystalline solid separates and this is colled and filtered. The solid consists of a mixture of colorless and yellow crystals that are separated manually to give 1.52g of a pale yellow solid, melting point 208° - 210°C. The yellow solid is recrystallized from 35ml of methoxyethanol to yield 1.22g of the title compound, melting point 212°-214°C.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 28 hours
  3. filtrationA crystalline solid separates and this is colled and filtered
  4. additionThe solid consists of a mixture of colorless and yellow crystals that
  5. customare separated manually

Sources & evidence

ORD record
ord-6a0f44e2b5ce4de6a7967d862f148455
Source dataset
uspto-grants-1976_01
Patent number
US03935197

Reaction notes

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