Aniline → 6-(2,6-dichlorophenyl)-8-methyl-2-(phenylamino)-7H,8H-pyrido[2,3-d]pyrimidin-7-one

HRID 3193

반응식

HRID 3193 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[C:22](=[O:23])[N:21]([CH3:24])[C:12]2[N:13]=[C:14](S(C)(=O)=O)[N:15]=[CH:16][C:11]=2[CH:10]=1.[NH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[C:22](=[O:23])[N:21]([CH3:24])[C:12]2[N:13]=[C:14]([NH:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[N:15]=[CH:16][C:11]=2[CH:10]=1

참가 물질

3

반응물 2

HCID 6115AnilineHCID 105961576-(2,6-Dichlorophenyl)-8-methyl-2-methylsulfonyl-8H-pyrido[2,3-d]pyrimidin-7-one

생성물 1

HCID 53278856-(2,6-dichlorophenyl)-8-methyl-2-(phenylamino)-7H,8H-pyrido[2,3-d]pyrimidin-7-one

반응 조건

온도
184 °C

실험 절차

A solution of 0.113 g (0.29 mmol) of 6-(2,6-dichlorophenyl)-2-methanesulfonyl-8-methyl-8H-pyrido[2,3-d]pyrimidin-7-one of Example 39 in 1.00 g (10.70 mmol) of aniline was maintained at reflux (184° C.) for 3 minutes. Most of the excess aniline was evaporated at reduced pressure. The remaining gum was dissolved in 1.0 mL of ethyl acetate. Crystals developed on inducement; wt 0.088 g. Further purification to remove dark colors was effected by silica gel chromatography, eluting with chloroform and then 50% hexane-ethyl acetate to obtain pure crystalline product; wt 0.046 g; mp 247°-249° C.

후처리

  1. customMost of the excess aniline was evaporated at reduced pressure
  2. dissolutionThe remaining gum was dissolved in 1.0 mL of ethyl acetate
  3. customFurther purification
  4. customto remove dark colors
  5. washeluting with chloroform
  6. custom50% hexane-ethyl acetate to obtain pure crystalline product

출처 및 근거

ORD 기록
ord-0aaab490559345e3a5659881e04302db
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05733914

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