Sodium Azide → 9-Allyl-6-pentyl-6,9-dihydro-5H-tetrazolo[5,1-i]purin-5-one

HRID 600580노트

반응식

HRID 600580 반응식
[CH2:1]([N:4]1[C:12]2[C:11](Cl)=[N:10][C:9](=[O:14])[N:8]([CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[C:7]=2[N:6]=[CH:5]1)[CH:2]=[CH2:3].[N-:20]=[N+:21]=[N-:22].[Na+]>C(O)C>[CH2:1]([N:4]1[C:12]2[C:11]3=[N:20][N:21]=[N:22][N:10]3[C:9](=[O:14])[N:8]([CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[C:7]=2[N:6]=[CH:5]1)[CH:2]=[CH2:3]

참가 물질

4

반응물 2

HCID 33557Sodium AzideHCID 598538197-Allyl-6-chloro-3-pentyl-3,7-dihydro-2H-purin-2-one

생성물 1

HCID 598538529-Allyl-6-pentyl-6,9-dihydro-5H-tetrazolo[5,1-i]purin-5-one수율 22.7%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A mixture of 7-allyl-6-chloro-3-pentyl-3,7-dihydro-2H-purin-2-one (0.65 g, 2.3 mmol) and sodium azide (0.98 g, 15 mmol) in ethanol (20 mL) was refluxed overnight. The reaction mixture was concentrated under vacuum. The residue was diluted with water and EtOAc. The organic phase was separated and the aqueous layer was extracted with EtOAc twice. The combined organic layers were dried over Na2SO4, filtered and concentrated to give the crude product, which was purified by preparative LCMS to provide the desired product as a white powder (0.15 g, 22.6%). LCMS calculated for C13H18N7O (M+H): 288.2. found: 288.1.

후처리

  1. temperaturewas refluxed overnight
  2. concentrationThe reaction mixture was concentrated under vacuum
  3. additionThe residue was diluted with water and EtOAc
  4. customThe organic phase was separated
  5. extractionthe aqueous layer was extracted with EtOAc twice
  6. dry with materialThe combined organic layers were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give the crude product, which
  10. customwas purified by preparative LCMS

출처 및 근거

ORD 기록
ord-ad7c2f61b2ee4bb38521630e8b5090b9
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07902205B2

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