Ethyl 2-[(3-methoxyphenyl)methylidene]-3-oxobutanoate → HCID 131717850, compound

HRID 1590286Notes

Reaction equation

HRID 1590286 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([C:16](=O)[CH3:17])[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:6]=[CH:7][CH:8]=1.Cl.[CH3:20][O:21][C:22]1[CH:32]=[CH:31][C:25]([CH2:26][S:27][C:28](=[NH:30])[NH2:29])=[CH:24][CH:23]=1.C([O-])(=O)C.[Na+]>CN(C)C=O.CCOCC>[CH3:20][O:21][C:22]1[CH:23]=[CH:24][C:25]([CH2:26][S:27][C:28]2[NH:30][C:16]([CH3:17])=[C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:9]([C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=3)[N:29]=2)=[CH:31][CH:32]=1

Participants

6

Reactant 3

HCID 367496Ethyl 2-[(3-methoxyphenyl)methylidene]-3-oxobutanoateHCID 517045Sodium AcetateHCID 13885856(4-Methoxyphenyl)methyl carbamimidothioate--hydrogen chloride (1/1)

Product 1

HCID 131717850HCID 131717850, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-[(3-methoxyphenyl)methylene]-3-oxobutanoic acid, ethyl ester (2.0 g., 8 mmole), S-(4-methoxybenzyl)thiopseudourea, hydrochloride (1.87 g., 8 mmole), and sodium acetate (0.67 g., 8 mmole) in dimethylformamide (10 ml.) is stirred at 70° for 4 hours. The cooled mixture is diluted with ether and washed with water, sodium bicarbonate, and brine. The dried solution is evaporated to give 2.85 g. of an impure oil. Flash chromatography using ethyl acetate:hexanes (1:3) gives 2.0 g. of 1,4-dihydro-2-[[(4-methoxyphenyl)methyl]thio]-4-(3-methoxyphenyl)- 6-methyl-5-pyrimidinedicarboxylic acid, ethyl ester as an oil.

Workup

  1. washwashed with water, sodium bicarbonate, and brine
  2. customThe dried solution is evaporated
  3. customto give 2.85 g
  4. customgives 2.0 g

Sources & evidence

ORD record
ord-34fba6b73b6d4758ab0652e93199f038
Source dataset
uspto-grants-1993_04
Patent number
US05202330

Reaction notes

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