Methyl iodide → HCID 22404769, compound

HRID 440698Notes

Reaction equation

HRID 440698 reaction equation
[Cl:1][C:2]1[C:7]2[CH:8]=[CH:9][C:10]([CH3:13])([CH3:12])[O:11][C:6]=2[C:5]([N:14]=[C:15]=[O:16])=[C:4]([F:17])[CH:3]=1.[H-].[Na+].[NH2:20]/[C:21](/[C:28]([F:31])([F:30])[F:29])=[CH:22]\[C:23](OCC)=[O:24].CI.[C:34](=O)([O-])[O-].[K+].[K+]>O1CCCC1>[Cl:1][C:2]1[C:7]2[CH:8]=[CH:9][C:10]([CH3:13])([CH3:12])[O:11][C:6]=2[C:5]([N:14]2[C:23](=[O:24])[CH:22]=[C:21]([C:28]([F:31])([F:30])[F:29])[N:20]([CH3:34])[C:15]2=[O:16])=[C:4]([F:17])[CH:3]=1

Participants

7

Reactant 5

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 24758Sodium hydrideHCID 5702529Ethyl 3-amino-4,4,4-trifluorocrotonateHCID 22404796HCID 22404796, compound

Product 1

HCID 22404769HCID 22404769, compoundYield 74.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

By the method of Example 1, Step G, 1.4 grams (0.005 mole) of 5-chloro-2,2-dimethyl-7-fluoro-2H-1-benzopyran-8-yl isocyanate was reacted with 0.3 gram (0.008 mole) of sodium hydride and 1.1 grams (0.006 mole) of ethyl 3-amino-4,4,4-trifluorocrotonate in 100 mL of tetrahydrofuran. Subsequently, 1.6 grams (0.011 mole) of methyl iodide and 1.5 grams (0.011 mole) of potassium carbonate were reacted with the product of the first reaction. The crude reaction product was purified by column chromatography on silica gel, with 1:9 methylene chloride:hexane and pure methylene chloride as eluants. The product-containing fractions were combined and concentrated under reduced pressure, yielding 1.5 grams of 3-(5-chloro-2,2-dimethyl-7-fluoro-2H-1-benzopyran-8-yl)-1-methyl-6-trifluoromethyluracil. The NMR spectrum was consistent with the proposed structure.

Workup

  1. customThe crude reaction product
  2. customwas purified by column chromatography on silica gel, with 1:9 methylene chloride
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-258561a8211440be9f6b19a1fe50d44d
Source dataset
uspto-grants-1996_05
Patent number
US05521147

Reaction notes

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