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2-(Methylthio)-4-(trimethylstannyl)pyrimidine → 6-(2-Furyl)-5-[2-(methylthio)pyrimidin-4-yl]pyrazin-2-amine

HRID 1710694
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HRID 1710694 반응식
Br[C:2]1[N:3]=[CH:4][C:5]([NH2:13])=[N:6][C:7]=1[C:8]1[O:9][CH:10]=[CH:11][CH:12]=1.[CH3:14][S:15][C:16]1[N:21]=[C:20]([Sn](C)(C)C)[CH:19]=[CH:18][N:17]=1>C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.CN(C)C=O>[O:9]1[CH:10]=[CH:11][CH:12]=[C:8]1[C:7]1[N:6]=[C:5]([NH2:13])[CH:4]=[N:3][C:2]=1[C:18]1[CH:19]=[CH:20][N:21]=[C:16]([S:15][CH3:14])[N:17]=1
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참가 물질

5

반응물 2

HCID 112662292-(Methylthio)-4-(trimethylstannyl)pyrimidineHCID 594576565-Bromo-6-(2-furyl)pyrazin-2-amine

생성물 1

HCID 160716596-(2-Furyl)-5-[2-(methylthio)pyrimidin-4-yl]pyrazin-2-amine수율 47%

시약·촉매·용매 2

HCID 6102075Dichlorobis(triphenylphosphine)palladium촉매HCID 6228Dimethylformamide
용매

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온도
150 °C

실험 절차

A microwave oven reactor was charged with 5-bromo-6-furan-2-ylpyrazin-2-ylamine (Preparation 2, 220 mg, 0.91 mmol), 2-methylsulfanyl-4-trimethylstannanylpyrimidine* (500 mg, 1.74 mmol), bis-(triphenylphosphin)palladium (II) chloride (60 mg, 0.08 mmol) and dimethylformamide (2.5 mL). The mixture was heated at 150° C. for 10 min in the microwave oven, then cooled, partitioned between water and ethyl acetate, the aqueous phase extracted twice with ethyl acetate, the organic layers washed with brine, dried (MgSO4) and evaporated. Flash chromatography (dichloromethane to dichloromethane/methanol 95:5) gave the title compound as a yellowish solid (123 mg, 47%). *Prepared according to Sandosham J.; Undheim, K. Tetrahedron 1994, 50 (1), 275-284.

후처리

  1. temperaturecooled
  2. custompartitioned between water and ethyl acetate
  3. extractionthe aqueous phase extracted twice with ethyl acetate
  4. washthe organic layers washed with brine
  5. dry with materialdried (MgSO4)
  6. customevaporated

출처 및 근거

ORD 기록
ord-5a9cc99e8adb4eaca29c6fafc30b2455
출처 데이터셋
uspto-grants-2010_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07790728B2

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