3-Aminopyridine → 2-[6-(3-Methoxyphenyl)-4-(3-pyridylamino)pyrimidin-2-yl]-1-morpholin-4-ylethan-1-one

HRID 499038ノート

反応式

HRID 499038 の反応式
C([O-])([O-])=O.[Cs+].[Cs+].FC(S(O[C:15]1[CH:20]=[C:19]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH3:28])[CH:22]=2)[N:18]=[C:17]([CH2:29][C:30]([N:32]2[CH2:37][CH2:36][O:35][CH2:34][CH2:33]2)=[O:31])[N:16]=1)(=O)=O)(F)F.[NH2:38][C:39]1[CH:40]=[N:41][CH:42]=[CH:43][CH:44]=1>C1COCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:28][O:27][C:23]1[CH:22]=[C:21]([C:19]2[N:18]=[C:17]([CH2:29][C:30]([N:32]3[CH2:37][CH2:36][O:35][CH2:34][CH2:33]3)=[O:31])[N:16]=[C:15]([NH:38][C:39]3[CH:40]=[N:41][CH:42]=[CH:43][CH:44]=3)[CH:20]=2)[CH:26]=[CH:25][CH:24]=1

参加物

6

反応物 3

HCID 100093-AminopyridineHCID 10796Cesium carbonateHCID 597897656-(3-Methoxyphenyl)-2-(2-morpholin-4-yl-2-oxoethyl)pyrimidin-4-yl (trifluoromethyl)sulfonate

生成物 1

HCID 597896702-[6-(3-Methoxyphenyl)-4-(3-pyridylamino)pyrimidin-2-yl]-1-morpholin-4-ylethan-1-one

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 8028Tetrahydrofuran溶媒

実験手順

A round bottom flask, oven dried and kept under N2 atmosphere is charged with Cs2CO3 (1.4 eq), Pd(OAc)2 (5 mol %), and S-(−)-BINAP (7.5 mol %). The flask is purged with N2 for about 5-10 min and a solution of compound 9 (1 eq) in dry THF is added via a syringe, followed by 3-aminopyridine (2 eq) in one portion. The flask is equipped with a reflux condenser, purged again with N2 for 5 min and the reaction mixture is refluxed overnight. The reaction mixture is cooled down to room temperature and the solvent is evaporated under reduced pressure. The residue is washed with water (×2) and triturated with methanol to afford the desired 2-[6-(3-methoxyphenyl)-4-(3-pyridylamino)pyrimidin-2-yl]-1-morpholin-4-ylethan-1-one 10.

後処理

  1. customA round bottom flask, oven dried
  2. customThe flask is purged with N2 for about 5-10 min
  3. customThe flask is equipped with a reflux condenser
  4. custompurged again with N2 for 5 min
  5. temperaturethe reaction mixture is refluxed overnight
  6. customthe solvent is evaporated under reduced pressure
  7. washThe residue is washed with water (×2)
  8. customtriturated with methanol

出典と根拠

ORDレコード
ord-fb4dfe9b60824191ae2434c4cc391ccc
出典データセット
uspto-grants-2010_08
特許番号
US07767669B2

反応ノート

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