Dimethylformamide → N'-(7-Chloro-6-(4-methoxyphenyl)-pyrido[2,3-d]pyrimidin-2-yl)-N,N-dimethyl-formamidine

HRID 617921ノート

反応式

HRID 617921 の反応式
[NH2:1][C:2]1[N:3]=[CH:4][C:5]2[CH:11]=[C:10]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=3)[C:9](O)=[N:8][C:6]=2[N:7]=1.ClCCl.S(Cl)([Cl:26])=O.[CH3:28][N:29]([CH3:32])[CH:30]=O>>[Cl:26][C:9]1[C:10]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)=[CH:11][C:5]2[CH:4]=[N:3][C:2]([N:1]=[CH:28][N:29]([CH3:32])[CH3:30])=[N:7][C:6]=2[N:8]=1

参加物

5

反応物 4

HCID 6228DimethylformamideHCID 6344DichloromethaneHCID 24386Thionyl ChlorideHCID 1784184612-Amino-6-(4-methoxyphenyl)-pyrido[2,3-d]pyrimidin-7-ol

生成物 1

HCID 53718994N'-(7-Chloro-6-(4-methoxyphenyl)-pyrido[2,3-d]pyrimidin-2-yl)-N,N-dimethyl-formamidine

実験手順

To a mixture of 67.0 g of 2-amino-6-(4-methoxyphenyl)-pyrido[2,3-d]pyrimidin-7-ol from Example 10, 1 L of dichloromethane, and 155 mL of dimethylformamide was added dropwise with cooling 72 mL of thionyl chloride keeping the temperature below 15° C. The suspension was heated to reflux with stirring for 6 hours. The reaction mixture was filtered and the filtrate evaporated in vacuo maintaining the temperature below 60° C. The resulting residue was dissolved in ice water and aqueous sodium hydroxide added with ice. The product was taken up in chloroform, washed with water, dried over anhydrous potassium carbonate, and evaporated. The residue was slurried with acetonitrile and the insoluble product collected by filtration to afford 31 g of the title compound N'-(7-chloro-6-(4-methoxyphenyl)-pyrido[2,3-d]pyrimidin-2-yl)-N,N-dimethyl-formamidine. The product was used in the next step without further purification.

後処理

  1. additionwas added dropwise
  2. temperatureThe suspension was heated
  3. temperatureto reflux
  4. filtrationThe reaction mixture was filtered
  5. customthe filtrate evaporated in vacuo
  6. temperaturemaintaining the temperature below 60° C
  7. dissolutionThe resulting residue was dissolved in ice water
  8. additionaqueous sodium hydroxide added with ice
  9. washwashed with water
  10. dry with materialdried over anhydrous potassium carbonate
  11. customevaporated
  12. filtrationthe insoluble product collected by filtration

出典と根拠

ORDレコード
ord-e115b60ad7e44acfa345123300f578e1
出典データセット
uspto-grants-1999_09
特許番号
US05952342

反応ノート

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