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Sodium Carbonate → 4-(4-((4-Chloro-1H-pyrazol-1-yl)methyl)benzyl)-2-(3-chlorophenyl)-6-ethylpyrimidine

HRID 1508886
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HRID 1508886 반응식
Cl[C:2]1[CH:7]=[C:6]([CH2:8][CH3:9])[N:5]=[C:4]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[CH:11]=2)[N:3]=1.[Cl:17][C:18]1[CH:19]=[N:20][N:21]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([CH2:30]B3OC(C)(C)C(C)(C)O3)=[CH:26][CH:25]=2)[CH:22]=1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Cl:17][C:18]1[CH:19]=[N:20][N:21]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([CH2:30][C:2]3[CH:7]=[C:6]([CH2:8][CH3:9])[N:5]=[C:4]([C:10]4[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[CH:11]=4)[N:3]=3)=[CH:26][CH:25]=2)[CH:22]=1
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참가 물질

7

반응물 3

HCID 10340Sodium CarbonateHCID 435575804-Chloro-2-(3-chlorophenyl)-6-ethylpyrimidineHCID 901100874-chloro-1-(4-((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl)benzyl)-1H-pyrazole

생성물 1

HCID 901128814-(4-((4-Chloro-1H-pyrazol-1-yl)methyl)benzyl)-2-(3-chlorophenyl)-6-ethylpyrimidine수율 43%

시약·촉매·용매 3

HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
촉매
HCID 962Water용매
HCID 312751,4-Dioxane용매

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온도
90 °C

실험 절차

A mixture of 4-chloro-2-(3-chlorophenyl)-6-ethylpyrimidine (0.100 g, 0.40 mmol), 4-chloro-1-(4-((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl)benzyl)-1H-pyrazole (0.197 g, 0.59 mmol), Pd(dppf)Cl2 (0.032 g, 0.04 mmol), and powdered Na2CO3 (0.126 g, 1.19 mmol) in dioxane (2.4 mL) and water (1.6 mL) was stirred under an argon atmosphere at 90° C. for 6 h, cooled, and filtered through celite with ethyl acetate washing. The filtrate was washed with saturated sodium chloride (3×25 mL), dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was purified by column chromatography (silica, hexane/dichloromethane) to afford the title compound (0.043 g, 43%) as a yellow oil. MW=423.34. 1H NMR (DMSO-d6, 500 MHz) δ 8.38-8.32 (m, 2H), 8.05 (s, 1H), 7.62-7.50 (m, 3H), 7.35 (d, J=8.1 Hz, 2H), 7.25 (s, 1H), 7.20 (d, J=8.1 Hz, 2H), 5.25 (s, 2H), 4.11 (s, 2H), 2.77 (q, J=7.6 Hz, 2H), 1.26 (t, J=7.6 Hz, 3H); APCI MS m/z 423 [M+H]+.

후처리

  1. temperaturecooled
  2. filtrationfiltered through celite with ethyl acetate washing
  3. washThe filtrate was washed with saturated sodium chloride (3×25 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography (silica, hexane/dichloromethane)

출처 및 근거

ORD 기록
ord-f11c33d676b44ffda70e1f9c48eadd90
출처 데이터셋
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09221843B2

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