2-Pyrrolidone → 1-{4-[2-(3-Chloro-phenylamino)-pyrimidin-4-yl]-pyridin-2-yl}-pyrrolidin-2-one

HRID 1791134ノート

反応式

HRID 1791134 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[N:14]=[C:13]([C:15]3[CH:20]=[CH:19][N:18]=[C:17](Cl)[CH:16]=3)[CH:12]=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].[NH:24]1[CH2:28][CH2:27][CH2:26][C:25]1=[O:29]>>[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[N:14]=[C:13]([C:15]3[CH:20]=[CH:19][N:18]=[C:17]([N:24]4[CH2:28][CH2:27][CH2:26][C:25]4=[O:29])[CH:16]=3)[CH:12]=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1

参加物

4

反応物 3

HCID 120252-PyrrolidoneHCID 24758Sodium hydrideHCID 9905031N-(3-chlorophenyl)-4-(2-chloropyridin-4-yl)pyrimidin-2-amine

生成物 1

HCID 220278791-{4-[2-(3-Chloro-phenylamino)-pyrimidin-4-yl]-pyridin-2-yl}-pyrrolidin-2-one

実験手順

To a solution of (3-chloro-phenyl)-[4-(2-chloro-pyridin-4-yl)-pyrimidin-2-yl]-amine (4.8 g, 0.015 mol) in pyrrolidon (20 ml) is added sodium hydride (1.93 g, 0.06 mmol of a 75% dispersion in oil) in several portions. The reaction temperature is slowly raised to +150° C. After 30 minutes the heating bath is removed and the mixture is poured onto crushed ice. The reaction mixture is partitioned between ethyl acetate and water. The organic phase is separated, dried over magnesium sulfate, filtered and evaporated under reduced presssure. The residue is purified by silicagel chromatography and recrystallized from ethyl acetate to give the title compound, m.p. 165–166° C.

後処理

  1. temperatureThe reaction temperature is slowly raised to +150° C
  2. customAfter 30 minutes the heating bath is removed
  3. additionthe mixture is poured
  4. customonto crushed ice
  5. customThe reaction mixture is partitioned between ethyl acetate and water
  6. customThe organic phase is separated
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated under reduced presssure
  10. customThe residue is purified by silicagel chromatography
  11. customrecrystallized from ethyl acetate

出典と根拠

ORDレコード
ord-3e32834ca23542119a7a7a66f6b9d3a3
出典データセット
uspto-grants-2006_07
特許番号
US07074787B2

反応ノート

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