Water → 1-methyl-6-trifluoromethyl-3-(6-amino4-chloro-2-fluoro-5-hydroxyphenyl)-2,4(1H,3H)-pyrimidinedione

HRID 1421460Notes

Reaction equation

HRID 1421460 reaction equation
[CH3:1][N:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][C:5](=[O:12])[N:4]([C:13]2[C:18]([N+:19]([O-])=O)=[C:17]([OH:22])[C:16]([Cl:23])=[CH:15][C:14]=2[F:24])[C:3]1=[O:25].O>C(O)(=O)C.[Fe]>[CH3:1][N:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][C:5](=[O:12])[N:4]([C:13]2[C:18]([NH2:19])=[C:17]([OH:22])[C:16]([Cl:23])=[CH:15][C:14]=2[F:24])[C:3]1=[O:25]

Participants

5

Reactant 2

HCID 962WaterHCID 183150861-methyl-6-trifluoromethyl-3-(4-chloro-2-fluoro-5-hydroxy-6-nitrophenyl)-2,4(1H,3H)-pyrimidinedione

Product 1

HCID 120569121-methyl-6-trifluoromethyl-3-(6-amino4-chloro-2-fluoro-5-hydroxyphenyl)-2,4(1H,3H)-pyrimidinedioneYield 70.7%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

This compound was prepared in the manner of Step B of Example 1, using 1.5 grams (0.004 mole) 1-methyl-6-trifluoromethyl-3-(4-chloro-2-fluoro-5-hydroxy-6-nitrophenyl)-2,4(1H,3H)-pyrimidinedione, 3.0 grams (0.054 mole) of iron dust, and 5 mL of water in 50 mL of glacial acetic acid, yielding 1.0 gram of title compound. The NMR spectrum was consistent with the proposed structure.

Workup

  1. customThis compound was prepared in the manner of Step B of Example 1

Sources & evidence

ORD record
ord-991690466f514f67b8eb3ef763424d35
Source dataset
uspto-grants-2000_06
Patent number
US06077812

Reaction notes

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