Benzamidine → HCID 178437564, compound

HRID 1779887Notes

Reaction equation

HRID 1779887 reaction equation
[C:1]([NH2:9])(=[NH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:10][C:11](=[CH:14][CH2:15][CH3:16])[CH:12]=[O:13]>CC(C)=O>[CH2:15]([CH:14]1[N:9]=[C:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[NH:8][CH:12]([OH:13])[CH:11]1[CH3:10])[CH3:16]

Participants

4

Reactant 2

HCID 2332BenzamidineHCID 121772-Methyl-2-pentenal

Product 1

HCID 178437564HCID 178437564, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

To an ice cooled mixture of 19.98 g (16.6 mmol) of benzamidine in 80 mL of acetone, was added dropwise over two hours, a solution of 16.35g (16.6 mmol) 2-methyl-2-pentenal and 0.055 g 1,4-hydroquinone, in acetone. The mixture was left to stir cold and warm to room temperature over 20 hours. The product was isolated by vacuum filtration and was washed with a minimal amount of acetone. 15.6 g (44%) of 6-ethyl-5-methyl-4-hydroxy-2-phenyl-3,4,5,6-tetrahydropyrimidine was collected, as a white solid.

Workup

  1. additionwas added dropwise over two hours
  2. waitThe mixture was left
  3. customThe product was isolated by vacuum filtration
  4. washwas washed with a minimal amount of acetone
  5. custom15.6 g (44%) of 6-ethyl-5-methyl-4-hydroxy-2-phenyl-3,4,5,6-tetrahydropyrimidine was collected, as a white solid

Sources & evidence

ORD record
ord-4de0c92578d94808a5d2cadd3f7cab9c
Source dataset
uspto-grants-1997_05
Patent number
US05629264

Reaction notes

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