Potassium Iodide → 6-[5-Bromo-2-(4-chloro-benzyloxy)-phenyl]-N*4*-(4-chloro-phenyl)-pyrimidine-2,4-diamine

HRID 28651

반응식

HRID 28651 반응식
[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[C:12]([Br:14])[CH:11]=[CH:10][C:9]=2[OH:15])[CH:5]=[C:4]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)[N:3]=1.[Cl:24][C:25]1[CH:32]=[CH:31][C:28]([CH2:29]Cl)=[CH:27][CH:26]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[K+]>C(#N)C>[Br:14][C:12]1[CH:11]=[CH:10][C:9]([O:15][CH2:29][C:28]2[CH:31]=[CH:32][C:25]([Cl:24])=[CH:26][CH:27]=2)=[C:8]([C:6]2[N:7]=[C:2]([NH2:1])[N:3]=[C:4]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=3)[CH:5]=2)[CH:13]=1

참가 물질

6

반응물 4

HCID 4875Potassium IodideHCID 77231-Chloro-4-(chloromethyl)benzeneHCID 10796Cesium carbonateHCID 1354366552-[2-Amino-6-(4-chloro-phenylamino)-pyrimidin-4-yl]-4-bromo-phenol

생성물 1

HCID 426071066-[5-Bromo-2-(4-chloro-benzyloxy)-phenyl]-N*4*-(4-chloro-phenyl)-pyrimidine-2,4-diamine수율 26%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
80 °C

실험 절차

To a stirred suspension of 2-[2-amino-6-(4-chloro-phenylamino) pyrimidin-4-yl]-4-bromo-phenol (0.059 g, 0.15 mmol), 4-chloro-benzylchloride (0.073 g, 0.45 mmol) and cesium carbonate (0.098 g, 0.30 mmol) in acetonitrile (10 ml) was added potassium iodide (40 mg). The mixture was stirred at 80° C. for 2 hours. Filtration and concentration of the filtrate provided a crude product which was purified by preparative TLC eluting with ethyl acetate-hexane (1:3) to provide the title compound (0.02 g, 26% yield). 1H NMR (CD3OD) δ 5.23 (s, 1H, CH2), 6.41 (s, 1H, Ar), 7.26 (d, 1H, J=9.6 Hz, Ar), 7.38-7.42 (m, 6H, Ar), 7.71-7.74 (m, 4H, Ar).

후처리

  1. filtrationFiltration and concentration of the filtrate
  2. customprovided a crude product which
  3. customwas purified by preparative TLC
  4. washeluting with ethyl acetate-hexane (1:3)

출처 및 근거

ORD 기록
ord-6475023d259c4c3c9410459e0ac6a9c4
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07419984B2

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