Methyl iodide → 3-(3-amino-4-chloro-6-fluoro-2-methoxyphenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione

HRID 275659

反応式

HRID 275659 の反応式
[NH2:1][C:2]1[C:3]([O:22][CH3:23])=[C:4]([N:10]2[C:15](=[O:16])[CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[NH:12][C:11]2=[O:21])[C:5]([F:9])=[CH:6][C:7]=1[Cl:8].[C:24](=O)([O-])[O-].[K+].[K+].CI>CC(C)=O>[NH2:1][C:2]1[C:3]([O:22][CH3:23])=[C:4]([N:10]2[C:15](=[O:16])[CH:14]=[C:13]([C:17]([F:19])([F:18])[F:20])[N:12]([CH3:24])[C:11]2=[O:21])[C:5]([F:9])=[CH:6][C:7]=1[Cl:8]

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 183150803-(3-amino4-chloro-6-fluoro-2-methoxyphenyl)-6-trifluoromethyl-2,4-(1H,3H)-pyrimidinedione

生成物 1

HCID 183150613-(3-amino-4-chloro-6-fluoro-2-methoxyphenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione収率 129.5%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

A solution of 7.5 grams (0.021 mole) of 3-(3-amino4-chloro-6-fluoro-2-methoxyphenyl)-6-trifluoromethyl-2,4-(1H,3H)-pyrimidinedione, 3.4 grams (0.025 mole) of potassium carbonate, and 3.5 grams (0.025 mole) of methyl iodide in 200 mL of acetone was stirred at ambient temperature for about 18 hours. The reaction mixture was then concentrated under reduced pressure, and the residue was taken up in 200 mL of water. The mixture was extracted with two 100 mL portions of ethyl acetate. The combined extracts were washed with two 50 mL portions of an aqueous saturated sodium chloride solution. The organic layer was dried with magnesium sulfate, filtered, and concentrated under reduced pressure, yielding 6.9 grams of crude product. The dark oil was combined with 7.0 grams of crude product prepared by a similar route to yield a total of 13.9 grams of crude product. The crude product was purified by column chromatography on silica gel, yielding 10.0 grams of title compound. The NMR spectrum was consistent with the proposed structure.

後処理

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. extractionThe mixture was extracted with two 100 mL portions of ethyl acetate
  3. washThe combined extracts were washed with two 50 mL portions of an aqueous saturated sodium chloride solution
  4. dry with materialThe organic layer was dried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customyielding 6.9 grams of crude product
  8. customprepared by a similar route
  9. customto yield a total of 13.9 grams of crude product
  10. customThe crude product was purified by column chromatography on silica gel

出典と根拠

ORDレコード
ord-03d7be7890fe48d6a9061387f99fe3e8
出典データセット
uspto-grants-2002_03
特許番号
US06352958B1

関連ノート

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