Methyl iodide → HCID 70300048, compound

HRID 1421852Notes

Reaction equation

HRID 1421852 reaction equation
[Cl:1][C:2]1[C:7]2[CH:8](C)[NH:9][O:10][C:6]=2[C:5]([N:12]2[C:17](=[O:18])[CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[NH:14][C:13]2=O)=[C:4]([F:24])[CH:3]=1.CI.[C:27](=[O:30])([O-])[O-].[K+].[K+].[CH2:33]1COCC1>O>[Cl:1][C:2]1[C:7]2[CH2:8][N:9]([CH3:33])[O:10][C:6]=2[C:5]([N:12]2[C:17](=[O:18])[CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[N:14]([CH3:13])[C:27]2=[O:30])=[C:4]([F:24])[CH:3]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 70298413HCID 70298413, compound

Product 1

HCID 70300048HCID 70300048, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 3-[4-chloro-6-fluoro-3-methyl-1,2(2H)-benzisoxazol-7-yl]-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (3.5 g, 0.010 mole), methyl iodide (2.1 g, 0.014 mole), potassium carbonate (2.0 g, 0.003 mole), and THF (100 mL) was heated to reflux where it stirred for five hours. The reaction mixture was then cooled to ambient temperature where it stirred for about 72 hours. After this time, the reaction mixture was poured into water and thoroughly extracted with ether. The combined extracts were washed with water and an aqueous saturated sodium chloride solution. The organic layer was separated, dried with magnesium sulfate, and concentrated to a residue. The residue was subjected to silica gel column chromatography using 9:1 to 5:1 hexane and ethyl acetate. The product-containing fractions provided 2.0 grams of Compound 27, m.p. 218-219° C. The NMR spectrum was consistent with the proposed structure.

Workup

  1. temperatureto reflux where it
  2. stirringstirred for about 72 hours
  3. extractionthoroughly extracted with ether
  4. washThe combined extracts were washed with water
  5. customThe organic layer was separated
  6. dry with materialdried with magnesium sulfate
  7. concentrationconcentrated to a residue

Sources & evidence

ORD record
ord-8e9726c8b2f1477aaac46a9033be56c5
Source dataset
uspto-grants-2000_06
Patent number
US06080702

Reaction notes

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