Cesium carbonate → 6-(2-nitro-5-(piperidin-1-yl)phenyl)-N-(1-(3-(trifluoromethyl)phenyl)-ethyl)pyrimidin-4-amine

HRID 625407노트

반응식

HRID 625407 반응식
Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[C:12]([N:14]3[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]3)[CH:11]=[CH:10][C:9]=2[N+:20]([O-:22])=[O:21])[N:5]=[CH:4][N:3]=1.[F:23][C:24]([F:35])([F:34])[C:25]1[CH:26]=[C:27]([CH:31]([NH2:33])[CH3:32])[CH:28]=[CH:29][CH:30]=1.C([O-])([O-])=O.[Cs+].[Cs+]>C1(C)C=CC=CC=1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>[N+:20]([C:9]1[CH:10]=[CH:11][C:12]([N:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)=[CH:13][C:8]=1[C:6]1[N:5]=[CH:4][N:3]=[C:2]([NH:33][CH:31]([C:27]2[CH:28]=[CH:29][CH:30]=[C:25]([C:24]([F:23])([F:34])[F:35])[CH:26]=2)[CH3:32])[CH:7]=1)([O-:22])=[O:21]

참가 물질

6

반응물 3

HCID 10796Cesium carbonateHCID 2782448(1R)-1-(3-(Trifluoromethyl)phenyl)ethylamineHCID 867059284-Chloro-6-(2-nitro-5-(piperidin-1-yl)phenyl)pyrimidine

생성물 1

HCID 665869426-(2-nitro-5-(piperidin-1-yl)phenyl)-N-(1-(3-(trifluoromethyl)phenyl)-ethyl)pyrimidin-4-amine수율 54.7%

시약·촉매·용매 2

HCID 634876Binap, (A+-)-촉매HCID 1140Toluene용매

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온도
120 °C

실험 절차

Into a 100 mL round bottom flask, was placed a solution of 4-chloro-6-(2-nitro-5-(piperidin-1-yl)phenyl)pyrimidine (100 mg, 0.31 mmol, 1.00 equiv) in toluene (10 mL), 1-(3-(trifluoromethyl)phenyl)ethanamine (71 mg, 0.38 mmol, 1.20 equiv), BINAP (9 mg, 0.01 mmol, 0.05 equiv), Cs2CO3 (144 mg, 0.44 mmol, 1.40 equiv), and Pd(dba)3CHCl3 (6.5 mg, 0.01 mmol, 0.02 equiv). The resulting solution was stirred for 3 h at 120° C. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column and eluted with ethyl acetate/petroleum ether (1:5). The product was obtained as 80 mg (54%) of a yellow oil.

후처리

  1. customInto a 100 mL round bottom flask, was placed
  2. concentrationThe resulting mixture was concentrated under vacuum
  3. washeluted with ethyl acetate/petroleum ether (1:5)

출처 및 근거

ORD 기록
ord-126ca3e30f9a42598c1d20170140d8c8
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09301951B2

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