Potassium Bromide → Ethyl 2-(4-fluorophenyl)-4-(methylthio)-1-[4-(methylthio)phenyl]-6-oxo-1,6-dihydropyrimidine-5-carboxylate

HRID 901931Notes

Reaction equation

HRID 901931 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][S:18][C:19]1[CH:24]=[CH:23][C:22]([NH:25][C:26]([C:28]2[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=2)=[NH:27])=[CH:21][CH:20]=1.[K+].[Br-]>>[F:34][C:31]1[CH:30]=[CH:29][C:28]([C:26]2[N:25]([C:22]3[CH:23]=[CH:24][C:19]([S:18][CH3:17])=[CH:20][CH:21]=3)[C:12](=[O:14])[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[C:3]([S:4][CH3:5])[N:27]=2)=[CH:33][CH:32]=1

Participants

4

Reactant 3

HCID 253877Potassium BromideHCID 35647452-(Bis-methylsulfanyl-methylene)-HCID 178503255HCID 178503255, compound

Product 1

HCID 69219248Ethyl 2-(4-fluorophenyl)-4-(methylthio)-1-[4-(methylthio)phenyl]-6-oxo-1,6-dihydropyrimidine-5-carboxylateYield 2.9%

Procedure

The title compound was prepared from diethyl [bis(methylthio)methylene]malonate (5.3 g, 20 mmol) and N-(4-methythiophenyl)-4-(fluoro)benzenecarboximidamide (5.2 g, 20 mmol) (prepared according to the procedure described in preparation 2) by following the procedure described in example 41 (0.25 g, yield 2.9%, mp 166-169° C., purity 96.84% by HPLC). 1H-NMR (CDCl3):δ 1.36-1.4 (t, 3H), 2.45 (s, 3H), 2.55 (s, 3H), 4.38-4.43 (q, 2H), 6.91-6.96 (m, 2H), 7.01-7.03 (d, 2H), 7.16-7.18 (d, 2H), 7.33-7.37 (m, 2H). IR (KBr) cm−1: 3447, 3069, 2989, 2900, 1733, 1666. MS m/z:431.2.0(M+).

Workup

  1. customprepared
  2. customdescribed in preparation 2)

Sources & evidence

ORD record
ord-1a02c37fb1ba4ab3a629be5ba85170dc
Source dataset
uspto-grants-2008_04
Patent number
US07365069B2

Reaction notes

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