Beta-Alanine → 5-[[4,6-Bis(1,1-dimethylethyl)-5-hydroxy-2-pyrimidinyl]methylene]-2-thioxo-4-thiazolidinone

HRID 2226427Notes

Reaction equation

HRID 2226427 reaction equation
[CH3:1][C:2]([C:5]1[C:10]([O:11]COCCOC)=[C:9]([C:18]([CH3:21])([CH3:20])[CH3:19])[N:8]=[C:7]([CH:22]=O)[N:6]=1)([CH3:4])[CH3:3].[S:24]1[CH2:30][C:28](=[O:29])[NH:27][C:25]1=[S:26].NCCC(O)=O>C(O)(=O)C.O>[CH3:3][C:2]([C:5]1[C:10]([OH:11])=[C:9]([C:18]([CH3:19])([CH3:21])[CH3:20])[N:8]=[C:7]([CH:22]=[C:30]2[S:24][C:25](=[S:26])[NH:27][C:28]2=[O:29])[N:6]=1)([CH3:4])[CH3:1]

Participants

6

Reactant 3

HCID 239Beta-AlanineHCID 1201546RhodanineHCID 199229924,6-Bis(1,1-dimethylethyl)-5-[(2-methoxyethoxy)methoxy]-2-pyrimidine carboxaldehyde

Product 1

HCID 539399305-[[4,6-Bis(1,1-dimethylethyl)-5-hydroxy-2-pyrimidinyl]methylene]-2-thioxo-4-thiazolidinone

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A mixture of 4,6-bis-(1,1-dimethylethyl)-5-[(2-methoxyethoxy)methoxy]-2-pyrimidine carboxaldehyde (0.5 g, 1.5 mmoles), rhodanine (0.25 g, 1.8 mmoles), and β-alanine (0.27 g, 3.1 mmoles) in acetic acid is heated at reflux for 1.5 hours. This solution is cooled to room temperature and diluted with 100 mL of water. The precipitate is collected by filtration and recrystallized from isopropyl ether/hexane. Yield of 5-[[4,6-bis-(1,1-dimethylethyl)-5-hydroxy-2-pyrimidinyl]methylene]-2-thioxo-4-thiazolidinone=0.26 g (48%). MP=257°-261° C. dec.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 1.5 hours
  3. filtrationThe precipitate is collected by filtration
  4. customrecrystallized from isopropyl ether/hexane

Sources & evidence

ORD record
ord-5ad00d4741414940b823eee29c704b21
Source dataset
uspto-grants-1994_09
Patent number
US05348957

Reaction notes

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