Beta-Alanine → 5-[(4,6-Ditert-butyl-5-hydroxypyrimidin-2-yl)methylidene]-2-imino-1,3-thiazolidin-4-one

HRID 2226428Notes

Reaction equation

HRID 2226428 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.COC1C=CC(/C=[C:45]2/[C:46]([NH:48][C:49]([S:51]/2)=[NH:50])=[O:47])=CC=1OC1CCCC1>>[CH3:1][C:2]([C:5]1[C:10]([OH:11])=[C:9]([C:18]([CH3:21])([CH3:20])[CH3:19])[N:8]=[C:7]([CH:22]=[C:45]2[S:51][C:49](=[NH:50])[NH:48][C:46]2=[O:47])[N:6]=1)([CH3:3])[CH3:4]

Participants

4

Reactant 3

HCID 239Beta-AlanineHCID 199229924,6-Bis(1,1-dimethylethyl)-5-[(2-methoxyethoxy)methoxy]-2-pyrimidine carboxaldehydeHCID 137629131(5Z)-5-[(3-cyclopentyloxy-4-methoxyphenyl)methylidene]-2-imino-1,3-thiazolidin-4-one

Product 1

HCID 1403692285-[(4,6-Ditert-butyl-5-hydroxypyrimidin-2-yl)methylidene]-2-imino-1,3-thiazolidin-4-oneYield 11.2%

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 pseudothiohydantoin (0.21 g, 1.8 mmoles) according to the procedure of Example 6 to give 0.056 g (11%) of 5-[[4,6-bis-(1,1-dimethylethyl]-5-hydroxy-pyrimidinyl]methylene]-2-imino-4-thiazolidinone. MP=278°-281° C. dec.

Sources & evidence

ORD record
ord-6a24855e4b154740b42796659d1606ca
Source dataset
uspto-grants-1994_09
Patent number
US05348957

Reaction notes

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