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

HRID 326677Notes

Reaction equation

HRID 326677 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-36ae538475694486af43e45375a22747
Source dataset
uspto-grants-1993_12
Patent number
US05270319

Reaction notes

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