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Triphenylphosphine → 2,6-Dichloro-9-cyclopropylpurine

HRID 452580
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HRID 452580 반응식
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][CH:7]=[N:8]2)=[C:4]([Cl:11])[N:3]=1.C1(P([C:25]2[CH:30]=[CH:29]C=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(O)CC1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>O1CCCC1>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH:29]2[CH2:30][CH2:25]2)=[C:4]([Cl:11])[N:3]=1
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참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 123361CyclopropanolHCID 53244122,6-DichloropurineHCID 5363146Diisopropyl azodicarboxylate

생성물 1

HCID 836813712,6-Dichloro-9-cyclopropylpurine수율 35%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

2,6-Dichloropurine (1 mmol), triphenylphosphine (1.3 mmol), tetrahydrofurane (5 ml) and cyclopropanol (5 mmol) were stirred at rt under nitrogen to give clear yellowish solution, which was then cooled to 0° C. and diisopropyldiazadicarboxylate (DIAD; 1.3 mmol) was added via syringe. The reaction mixture was then stirred at rt for 12 h. After evaporation of the solvents the product was extracted with diethylether and purified by column chromatography (silicagel, 1% MeOH in CHCl3). Crystallization from methanol gave the product in yield 35%, mp 121-124° C.

후처리

  1. customto give clear yellowish solution, which
  2. customAfter evaporation of the solvents the product
  3. extractionwas extracted with diethylether
  4. custompurified by column chromatography (silicagel, 1% MeOH in CHCl3)
  5. customCrystallization from methanol
  6. customgave the product in yield 35%, mp 121-124° C.

출처 및 근거

ORD 기록
ord-1588bcbed76247d18f369896691036af
출처 데이터셋
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08492391B2

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