N,N-dimethyl-p-phenylenediamine → C2 Pyrido[2,3-d]pyrimidin-7-one deriv. 31

HRID 2300082ノート

反応式

HRID 2300082 の反応式
[CH2:1]([N:3]1[C:8]2[N:9]=[C:10](S(C)=O)[N:11]=[CH:12][C:7]=2[CH:6]=[CH:5][C:4]1=[O:16])[CH3:2].[CH3:17][N:18]([CH3:26])[C:19]1[CH:25]=[CH:24][C:22]([NH2:23])=[CH:21][CH:20]=1>>[CH3:17][N:18]([CH3:26])[C:19]1[CH:25]=[CH:24][C:22]([NH:23][C:10]2[N:11]=[CH:12][C:7]3[CH:6]=[CH:5][C:4](=[O:16])[N:3]([CH2:1][CH3:2])[C:8]=3[N:9]=2)=[CH:21][CH:20]=1

参加物

3

反応物 2

HCID 7472N,N-dimethyl-p-phenylenediamineHCID 10752351Pyrido[2,3-d]pyrimidin-7(8H)-one, 8-ethyl-2-(methylsulfinyl)-

生成物 1

HCID 5330217C2 Pyrido[2,3-d]pyrimidin-7-one deriv. 31収率 50%

反応条件

温度
175 °C

実験手順

A mixture of 8-ethyl-2-methanesulfinyl-8H-pyrido[2,3-d]pyrimidin-7-one (155 mg, 0.65 mmol) and 500 μL of 4-dimethylaminoaniline was heated at 175° C. for 10 minutes, then cooled to room temperature and partitioned between saturated sodium bicarbonate and ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The resultant solid was washed with hexane and ethyl acetate then purified by flash chromatography eluting with ethyl acetate. The fractions containing product were concentrated and a 2:1 mixture of hexane and ethyl acetate was added to the residue. The resultant precipitate was collected by filtration to give 110 mg (50%) of 2-(4-dimethylamino-phenylamino)-8-ethyl-8H-pyrido[2,3-d]pyrimidin-7-one, mp 189-191° C.

後処理

  1. temperaturecooled to room temperature
  2. custompartitioned between saturated sodium bicarbonate and ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. washThe resultant solid was washed with hexane and ethyl acetate
  8. customthen purified by flash chromatography
  9. washeluting with ethyl acetate
  10. additionThe fractions containing product
  11. concentrationwere concentrated
  12. additiona 2:1 mixture of hexane and ethyl acetate
  13. additionwas added to the residue
  14. filtrationThe resultant precipitate was collected by filtration

出典と根拠

ORDレコード
ord-c258c07fe8264c3683bd7a261c76449c
出典データセット
uspto-grants-2002_12
特許番号
US06498163B1

反応ノート

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