3-(4-chloro-2-fluoro-5-nitrophenyl)-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione → 3-(5-amino-4-chloro-2-fluorophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione

HRID 380785Notes

Reaction equation

[Cl:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][C:5]([N:11]2[C:16](=[O:17])[CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[N:13]([CH3:22])[C:12]2=[O:23])=[C:4]([F:24])[CH:3]=1>C(O)(=O)C.O.[Fe]>[NH2:8][C:7]1[C:2]([Cl:1])=[CH:3][C:4]([F:24])=[C:5]([N:11]2[C:16](=[O:17])[CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[N:13]([CH3:22])[C:12]2=[O:23])[CH:6]=1

Participants

Conditions

Temperature: 55 °C

Procedure

A solution of 3-(4-chloro-2-fluoro-5-nitrophenyl)-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione (3.00 g, 8.16 mmol) in acetic acid is heated to 50-60° C., treated portionwise with iron powder (2.28 g, 40.8 mmol) over 10 minutes, stirred at 50-60° C. for 90 minutes, cooled to room temperature, and diluted with water. The resultant aqueous mixture is filtered to remove solids and extracted with diethyl ether. The organic extracts are combined, washed sequentially with 1 M sodium hydroxide solution and brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo to give the title product as a brown solid (2.37 g, 86% yield, mp 132-135° C.) which is identified by 1H and 13C NMR spectral analyses.

Workup

temperaturecooled to room temperature
filtrationThe resultant aqueous mixture is filtered
customto remove solids
extractionextracted with diethyl ether
washwashed sequentially with 1 M sodium hydroxide solution and brine
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-6435d8b0778d4155a3028c576946abdd
Source dataset: uspto-grants-2001_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06303783B1

Reaction notes

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