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

HRID 30443노트

반응식

HRID 30443 반응식
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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 8028Tetrahydrofuran용매

실험 절차

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 (x2) 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.

후처리

  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 (x2)
  8. customtriturated with methanol

출처 및 근거

ORD 기록
ord-6a688ba4a195419eafbcbf06c956da80
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07423148B2

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