Methyl iodide → Methyl 6-chloro-2-methyl-3-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-2,3-dihydropyrimidin-1(6H)-yl)benzoate

HRID 650908Notes

Reaction equation

HRID 650908 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[C:6]([CH3:12])[C:5]([N:13]2[C:18](=[O:19])[CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[NH:15][C:14]2=[O:24])=[CH:4][CH:3]=1.[C:25](=O)([O-])[O-].[K+].[K+].CI>C1COCC1>[Cl:1][C:2]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[C:6]([CH3:12])[C:5]([N:13]2[C:18](=[O:19])[CH:17]=[C:16]([C:20]([F:22])([F:21])[F:23])[N:15]([CH3:25])[C:14]2=[O:24])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 21710140Methyl 6-chloro-3-(2,6-dioxo-4-(trifluoromethyl)-2,3-dihydropyrimidin-1(6H)-yl)-2-methylbenzoate

Product 1

HCID 21710151Methyl 6-chloro-2-methyl-3-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-2,3-dihydropyrimidin-1(6H)-yl)benzoateYield 100.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

This compound was prepared in a manner analogous to Step E, Example 1. Here, 8.2 grams (0.0206 mole) of methyl 6-chloro-2-methyl-3-[6-trifluoromethyl-2,4(1H,3H)-pyrimidinedion-3-yl]benzoate was combined with 5.7 grams (0.410 mole) of potassium carbonate and 4.4 grams (0.309 mole) of methyl iodide in 200 mL of THF. The reaction product was purified by column chromatography on silica gel using mixtures of EtOAc and hexane as eluants. The fractions containing product were combined and concentrated under reduced pressure, yielding 7.8 grams of subject compound. The NMR spectrum was consistent with the proposed structure.

Workup

  1. customThis compound was prepared in a manner analogous to Step E, Example 1
  2. customThe reaction product was purified by column chromatography on silica gel using mixtures of EtOAc and hexane as eluants
  3. additionThe fractions containing product
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9eb32d49f8f74b1091a5a3a046f18168
Source dataset
uspto-grants-2001_08
Patent number
US06277847B1

Reaction notes

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