Acetic Acid → 2-aminopyrido[2,3-d]pyrimidin-7(8H)-one 54

HRID 3212

反応式

HRID 3212 の反応式
[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.[CH3:25][O:26][C:27]1[CH:28]=[C:29]([CH:31]=[C:32]([O:34][CH3:35])[CH:33]=1)[NH2:30].C(O)(=O)C>O>[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:30][C:29]3[CH:31]=[C:32]([O:34][CH3:35])[CH:33]=[C:27]([O:26][CH3:25])[CH:28]=3)[N:15]=[CH:16][C:11]=2[CH:10]=1

参加物

5

反応物 3

HCID 176Acetic AcidHCID 663013,5-DimethoxyanilineHCID 105961576-(2,6-Dichlorophenyl)-8-methyl-2-methylsulfonyl-8H-pyrido[2,3-d]pyrimidin-7-one

生成物 1

HCID 53279002-aminopyrido[2,3-d]pyrimidin-7(8H)-one 54

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
160 °C

実験手順

A mixture of 0.155 g (0.40 mmol) of 6-(2,6-dichlorophenyl)-2-methanesulfonyl-8-methyl-8H-pyrido[2,3-d]pyrimidin-7-one of Example 39 and 0.400 g (2.60 mmol) of 3,5-dimethoxyaniline was heated in a 160° C. oil bath for 5 minutes. At ca. 100° C., 1 mL of glacial acetic acid was added to the melt to dissolve. Water (10 mL) was added to precipitate a gum. Decanted and dissolved gum in 35 mL of methylene chloride. The solution was washed with 2×20 mL of water, dried over magnesium sulfate, charcoaled, filtered, and concentrated. The remaining gum was purified silica gel chromatography eluting with chloroform and then with 2:1 hexane:ethyl acetate to obtain the fraction containing the pure product. The eluent was evaporated to near dryness when crystals separated. The crystals were filtered and washed with 0.5 mL of ether; wt 0.059 g; mp 228°-230° C.

後処理

  1. dissolutionto dissolve
  2. customto precipitate a gum
  3. customDecanted
  4. dissolutiondissolved gum in 35 mL of methylene chloride
  5. washThe solution was washed with 2×20 mL of water
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe remaining gum was purified silica gel chromatography
  10. washeluting with chloroform
  11. customwith 2:1 hexane:ethyl acetate to obtain the fraction
  12. additioncontaining the pure product
  13. customThe eluent was evaporated
  14. customseparated
  15. filtrationThe crystals were filtered
  16. washwashed with 0.5 mL of ether

出典と根拠

ORDレコード
ord-8f36c1ceeca8456d85e3fbff6f422fe7
出典データセット
uspto-grants-1998_03
特許番号
US05733914

関連ノート

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