Aniline → (+/-)-3-(2-chloro-5-methoxy-phenyl)-4-methyl-1-phenyl-7-phenylamino-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one

HRID 2216986ノート

反応式

HRID 2216986 の反応式
Cl[C:2]1[N:7]=[C:6]2[N:8]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:9](=[O:22])[N:10]([C:13]3[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[CH:15][C:14]=3[Cl:21])[CH:11]([CH3:12])[C:5]2=[CH:4][N:3]=1.[NH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>>[Cl:21][C:14]1[CH:15]=[CH:16][C:17]([O:19][CH3:20])=[CH:18][C:13]=1[N:10]1[CH:11]([CH3:12])[C:5]2[C:6](=[N:7][C:2]([NH:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[N:3][CH:4]=2)[N:8]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:9]1=[O:22]

参加物

3

反応物 2

HCID 6115AnilineHCID 10431977HCID 10431977、化合物

生成物 1

HCID 10344724(+/-)-3-(2-chloro-5-methoxy-phenyl)-4-methyl-1-phenyl-7-phenylamino-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one

反応条件

温度
100 °C

実験手順

(±)-7-Chloro-3-(2-chloro-5-methoxy-phenyl)-4-methyl-1-phenyl-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one (0.20 g; 0.49 mmol) (from Example 12b supra) was combined with aniline (150 μL; 1.65 mmol) (Aldrich) and heated in an oil bath at 100° C. for about 70 minutes. Upon cooling, the residue was triturated with hexanes and then partitioned between ethyl acetate and water. The organic phase was washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated. The crude material was purified by flash chromatography (Biotage, 40M; 40:60 ethyl acetate-hexanes) to give (±)-3-(2-chloro-5-methoxy-phenyl)-4-methyl-1-phenyl-7-phenylamino-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one as a light yellow solid. (Yield 0.15 g; 63.7%).

後処理

  1. temperatureUpon cooling
  2. customthe residue was triturated with hexanes
  3. custompartitioned between ethyl acetate and water
  4. washThe organic phase was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude material was purified by flash chromatography (Biotage, 40M; 40:60 ethyl acetate-hexanes)

出典と根拠

ORDレコード
ord-5fe287b03b2d4683a7e9aa26c07cf77e
出典データセット
uspto-grants-2006_09
特許番号
US07112676B2

反応ノート

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