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

HRID 2374309ノート

反応式

HRID 2374309 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

HCID 598538529-Allyl-6-pentyl-6,9-dihydro-5H-tetrazolo[5,1-i]purin-5-one収率 22.6%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A mixture of 7-allyl-6-chloro-3-pentyl-3,7-dihydro-2H-purin-2-one (0.65 g, 2.3 mol) 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.

後処理

  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

出典と根拠

ORDレコード
ord-484abbc9d2104baaaa77abe5d7adba77
出典データセット
uspto-grants-2008_12
特許番号
US07462624B2

反応ノート

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