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Sodium Carbonate → HCID 58166641, 화합물

HRID 626692
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HRID 626692 반응식
[NH2:1][C:2]1[CH:7]=[C:6](Cl)[N:5]=[CH:4][N:3]=1.C(=O)([O-])[O-].[Na+].[Na+].O1CCO[CH2:17][CH2:16]1>O.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH:16]([C:6]1[N:5]=[CH:4][N:3]=[C:2]([NH2:1])[CH:7]=1)=[CH2:17]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 2380124-Amino-6-chloropyrimidine

생성물 1

HCID 58166641HCID 58166641, 화합물수율 80%

시약·촉매·용매 2

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

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온도
100 °C

실험 절차

A mixture of 4-amino-6-chloropyrimidine (2.5 g, 19.2 mmol), 1,1′-bis(diphenylphosphino)ferrocene palladium dichloride (810 mg, 1.2 mmol), sodium carbonate (8.14 g, 76.8 mmol) and vinyl borane pinacol ester (3.9 mL, 23 mmol) in dioxane (11.5 mL) and water (11.5 mL) under nitrogen, was heated at 100° C. for 20 hours then cooled to ambient temperature. The reaction mixture was partitioned between ethyl acetate and water. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography (0-10% methanol in DCM) to afford the title compound as a yellow solid (1.87 g, 80% yield). 1H NMR (300 MHz, DMSO-d6): δ 8.30 (s, 1H), 6.83 (s, 2H), 6.57 (dd, J=17.2, 10.5 Hz, 1H), 6.36 (s, 1H), 6.26 (dd, J=17.2, 2.1 Hz, 1H), 5.48 (dd, J=10.5, 2.1 Hz, 1H).

후처리

  1. temperaturethen cooled to ambient temperature
  2. customThe reaction mixture was partitioned between ethyl acetate and water
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel flash chromatography (0-10% methanol in DCM)

출처 및 근거

ORD 기록
ord-c7e200e202b84383b191c607a4d157fc
출처 데이터셋
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09309240B2

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