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

HRID 326679Notes

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].NCCC(O)=O.[S:30]1[CH2:34][C:33](=[O:35])[NH:32][C:31]1=[O:36]>>[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:34]2[S:30][C:31](=[O:36])[NH:32][C:33]2=[O:35])[N:6]=1)([CH3:1])[CH3:4]

Participants

Reactant 3

HCID 239Beta-Alanine

HCID 5437Thiazolidinedione

HCID 199229924,6-Bis(1,1-dimethylethyl)-5-[(2-methoxyethoxy)methoxy]-2-pyrimidine carboxaldehyde

Product 1

HCID 542646175-[[4,6-Bis-(1,1-dimethylethyl]-5 hydroxy-2-pyrimidinyl]methylene]-2,4-thiazolidinedioneYield 25%

Procedure

4,6-Bis-(1,1-dimethylethyl)-5-[(2-methoxyethoxy)methoxy]-2-pyrimidine carboxaldehyde (0.5 g, 1.5 mmoles) is treated with β-alanine (0.27 g, 3.1 mmoles) and 2,4-thiazolidinedione (0.22 g, 1.8 mmoles) according to the procedure of Example 6 to give 0.12 g (25%) of 5-[[4,6-bis-(1,1-dimethylethyl]-5 hydroxy-2-pyrimidinyl]methylene]-2,4-thiazolidinedione. MP=229°-232° C. dec.

Sources & evidence

ORD record: ord-81b905e574e548da857306ef7ddbab10
Source dataset: uspto-grants-1993_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05270319

Reaction notes

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