2-(Bis-methylsulfanyl-methylene)- → Ethyl 1-(4-methylphenyl)-4-(methylthio)-2-[4-(methylthio)phenyl]-6-oxo-1,6-dihydropyrimidine-5-carboxylate

HRID 901929Notes

Reaction equation

HRID 901929 reaction equation
CS[C:3](=[C:6]([C:12]([O:14]CC)=O)[C:7]([O:9][CH2:10][CH3:11])=[O:8])[S:4][CH3:5].[CH3:17][C:18]1[CH:23]=[CH:22][C:21]([NH:24][C:25]([C:27]2[CH:32]=[CH:31][C:30]([S:33][CH3:34])=[CH:29][CH:28]=2)=[NH:26])=[CH:20][CH:19]=1>>[CH3:17][C:18]1[CH:19]=[CH:20][C:21]([N:24]2[C:12](=[O:14])[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[C:3]([S:4][CH3:5])[N:26]=[C:25]2[C:27]2[CH:32]=[CH:31][C:30]([S:33][CH3:34])=[CH:29][CH:28]=2)=[CH:22][CH:23]=1

Participants

3

Reactant 2

HCID 35647452-(Bis-methylsulfanyl-methylene)-HCID 178503190HCID 178503190, compound

Product 1

HCID 59700949Ethyl 1-(4-methylphenyl)-4-(methylthio)-2-[4-(methylthio)phenyl]-6-oxo-1,6-dihydropyrimidine-5-carboxylateYield 20.2%

Conditions

Temperature
115 °C

Procedure

A mixture of diethyl [bis(methylthio)methylene]malonate (2.64 g, 10 mmol) and N-(4-methylphenyl)-4-(methylthio)benzenecarboximidamide (2.6 g, 10 mmol) (prepared according to the procedure described in preparation 6) was heated at 110-120° C. for 2 hours. The gummy mass thus obtained was purified by column chromatography to give the title compound (0.86 g, yield 20.2%, mp 153-155° C., purity 99.81% by HPLC). 1H-NMR (CDCl3):δ 1.36-1.39 (t, 3H), 2.33 (s, 3H), 2.44 (s, 3H), 2.55 (s, 3H), 4.37-4.42 (q, 2H), 7.0-7.05 (m, 4H), 7.13-7.15 (d, 2H), 7.25-7.27 (d, 2H). IR (KBr) cm−1: 2981, 2924, 1693 (—C═O). MS m/z:427.1(M+)

Workup

  1. customprepared
  2. customdescribed in preparation 6)
  3. customThe gummy mass thus obtained
  4. customwas purified by column chromatography

Sources & evidence

ORD record
ord-b8826c63c02e4841853837521efc38b8
Source dataset
uspto-grants-2008_04
Patent number
US07365069B2

Reaction notes

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