8-Oxa-bicyclo[3.2.1]oct-6-ene-3-carboxylic acid (6-amino-2,4-dioxo-1,3-dipropyl-1,2,3,4-tetrahydro-pyrimidin-5-yl)-amide → 8-(8-Oxa-bicyclo[3.2.1]oct-6-en-3-yl)-1,3-dipropyl-3,7-dihydro-purine-2,6-dione

HRID 395890노트

반응식

HRID 395890 반응식
[NH2:1][C:2]1[N:7]([CH2:8][CH2:9][CH3:10])[C:6](=[O:11])[N:5]([CH2:12][CH2:13][CH3:14])[C:4](=[O:15])[C:3]=1[NH:16][C:17]([CH:19]1[CH2:25][CH:24]2[O:26][CH:21]([CH:22]=[CH:23]2)[CH2:20]1)=O>[OH-].[Na+].CO>[CH:21]12[O:26][CH:24]([CH:23]=[CH:22]1)[CH2:25][CH:19]([C:17]1[NH:16][C:3]3[C:4](=[O:15])[N:5]([CH2:12][CH2:13][CH3:14])[C:6](=[O:11])[N:7]([CH2:8][CH2:9][CH3:10])[C:2]=3[N:1]=1)[CH2:20]2

참가 물질

4

반응물 1

HCID 865903668-Oxa-bicyclo[3.2.1]oct-6-ene-3-carboxylic acid (6-amino-2,4-dioxo-1,3-dipropyl-1,2,3,4-tetrahydro-pyrimidin-5-yl)-amide

생성물 1

HCID 102911968-(8-Oxa-bicyclo[3.2.1]oct-6-en-3-yl)-1,3-dipropyl-3,7-dihydro-purine-2,6-dione수율 58.1%

시약·촉매·용매 2

HCID 887Methanol용매HCID 14798Sodium Hydroxide용매

실험 절차

A solution of 8-oxa-bicyclo[3.2.1]oct-6-ene-3-carboxylic acid (6-amino-2,4-dioxo-1,3-dipropyl-1,2,3,4-tetrahydro-pyrimidin-5-yl)-amide (0.185 mmol, 0.067 g) in 20% NaOH (1.23 ml) and MeOH (6.2 ml) was stirred and refluxed overnight. The reaction was cooled to room temperature and then concentrated to remove MeOH. The aqueous residue was extracted with Et2O and these extracts discarded. The aqueous was acidified (pH 2-3) with conc. HCl and then extracted with EtOAc. The combined EtOAc extracts were washed with H2O and brine and dried (MgSO4). Filtration and evaporation followed by flash column chromatography, eluting with 1:1 EtOAc/CH2Cl2, provided the title compound (0.037 g, 58%) as a beige solid. 1H NMR (300 MHz, CDCl3): 0.93-0.99 (m, 6H), 1.62-1.83 (m, 6H), 2.14-2.25 (m, 2H), 3.40-3.51 (m, 1H), 4.05-1.10 (m, 4H), 4.86 (br s, 2H), 6.25 (s, 2H).

후처리

  1. temperaturerefluxed overnight
  2. concentrationconcentrated
  3. customto remove MeOH
  4. extractionThe aqueous residue was extracted with Et2O
  5. extractionextracted with EtOAc
  6. washThe combined EtOAc extracts were washed with H2O and brine
  7. dry with materialdried (MgSO4)
  8. filtrationFiltration and evaporation
  9. washeluting with 1:1 EtOAc/CH2Cl2

출처 및 근거

ORD 기록
ord-b2d8ec3403824642b5ffb25fea4b2fab
출처 데이터셋
uspto-grants-2003_08
특허 번호
US06605600B1

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