3-Bromo-3'-(trifluoromethyl)benzanilide → 3-[2-(methylthio)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl]-N-[3-(trifluoromethyl)phenyl]benzamide

HRID 338743노트

반응식

HRID 338743 반응식
Br[C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][CH:20]=1)[C:5]([NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=1)=[O:6].[CH3:21][S:22][C:23]1[N:24]=[CH:25][C:26]2[CH2:32][NH:31][CH2:30][CH2:29][C:27]=2[N:28]=1.CC(C)([O-])C.[Na+]>C1COCC1.CCOC(C)=O.CC(OC1C=CC=C(OC(C)C)C=1C1C(P(C2CCCCC2)C2CCCCC2)=CC=CC=1)C>[CH3:21][S:22][C:23]1[N:24]=[CH:25][C:26]2[CH2:32][N:31]([C:2]3[CH:3]=[C:4]([CH:18]=[CH:19][CH:20]=3)[C:5]([NH:7][C:8]3[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=3)=[O:6])[CH2:30][CH2:29][C:27]=2[N:28]=1

참가 물질

7

반응물 3

HCID 7638833-Bromo-3'-(trifluoromethyl)benzanilideHCID 23676156Sodium t-butoxideHCID 552636702-(Methylthio)-5,6,7,8-tetrahydropyrido[4,3-D]pyrimidine

생성물 1

HCID 717356913-[2-(methylthio)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl]-N-[3-(trifluoromethyl)phenyl]benzamide수율 80%

시약·촉매·용매 3

HCID 162179852-Dicyclohexylphosphino-2',6'-diisopropoxybiphenyl촉매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

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온도
80 °C

실험 절차

A mixture of 3-bromo-N-[3-(trifluoromethyl)phenyl]benzamide (379 mg, 1.10 mmol), 2-(methylsulfanyl)-5,6,7,8-tetrahydropyrido[4,3-d]-pyrimidine (200 mg, 1.10 mmol), RuPhos (15.4 mg, 0.033 mmol), Cl—RuPhos-Pd precatalyst (24 mg, 0.033 mmol), and sodium-t-butoxide (148 mg, 1.54 mmol) in anhydrous THF (30 ml) was heated at 80° C. under nitrogen for 21 hours. Upon cooling, the reaction mixture was diluted with EtOAc and the insolubles were filtered off (celite). The filtrate was concentrated and the residue was eluted through a flash column (silica gel 60, 230-400 mesh, 1:1 hexanes:EtOAc) to obtain a yellow, crystalline solid (389 mg, 80%).

후처리

  1. temperatureUpon cooling
  2. filtrationthe insolubles were filtered off (celite)
  3. concentrationThe filtrate was concentrated
  4. washthe residue was eluted through a flash column (silica gel 60, 230-400 mesh, 1:1 hexanes:EtOAc)

출처 및 근거

ORD 기록
ord-4649514306b84d4aa43865df107b4beb
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889870B2

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