Tetrahydrofuran → 3-Amino-1-cyclopropyl-6,7-difluoro-1H-quinazoline-2,4-dione

HRID 10327

反応式

HRID 10327 の反応式
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:15])=[C:11]([F:14])[CH:12]=3)[C:7](=[O:16])[NH:6][C:5]2=[O:17])[CH2:3][CH2:2]1.O1CCCC1.[H-].[Na+].[N+:25](C1C=C([N+]([O-])=O)C=CC=1NO)([O-])=O>CN(C)C=O.O1CCOCC1>[NH2:25][N:6]1[C:7](=[O:16])[C:8]2[C:13](=[CH:12][C:11]([F:14])=[C:10]([F:15])[CH:9]=2)[N:4]([CH:1]2[CH2:3][CH2:2]2)[C:5]1=[O:17]

参加物

7

反応物 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 5743493N-Hydroxy-2,4-dinitrobenzenamineHCID 112764481-Cyclopropyl-6,7-difluoroquinazoline-2,4(1H,3H)-dione

生成物 1

HCID 114821773-Amino-1-cyclopropyl-6,7-difluoro-1H-quinazoline-2,4-dione

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
50 °C

実験手順

To a solution of a 1-cyclopropyl-6,7-difluoro-1H-quinazoline-2,4-dione (Example 23) in 1:1 dry tetrahydrofuran or dioxane and dry N,N-dimethylformamide is added portionwise sodium hydride (1.1 eq., 60% mineral oil dispersion) at room temperature. After stirring at 50° C. for 20 to 30 minutes, the resulting solution is cooled to room temperature and 2,4-dinitrophenylhydroxylamine (4 eq.) is added. The mixture is heated at 60° C. to 80° C. for 30 minutes, cooled, and the dioxane removed reduced pressure. The residue is poured into ice water and extracted with ethyl acetate. The organic layers are combined, washed with brine, dried with Na2SO4, and concentrated in vacuo. The residue is purified by flash column chromatography (ethyl acetate/hexanes) to afford a 3-amino-1-cyclopropyl-6,7-difluoro-1H-quinazoline-2,4-dione.

後処理

  1. temperaturethe resulting solution is cooled to room temperature
  2. temperatureThe mixture is heated at 60° C. to 80° C. for 30 minutes
  3. temperaturecooled
  4. customthe dioxane removed reduced pressure
  5. additionThe residue is poured into ice water
  6. extractionextracted with ethyl acetate
  7. washwashed with brine
  8. dry with materialdried with Na2SO4
  9. concentrationconcentrated in vacuo
  10. customThe residue is purified by flash column chromatography (ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-9b30bb348856466e831c1ac5c92d19a5
出典データセット
uspto-grants-2006_08
特許番号
US07094780B1

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