6-Chloro-9-[2-(2,2-dimethyl-1,3-dioxan-5-yl)ethyl]-9H-purin-2-amine → 6-Deoxypenciclovir

HRID 5865

반응식

HRID 5865 반응식
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:11][CH2:12][CH:13]2[CH2:18][O:17]C(C)(C)[O:15][CH2:14]2)=[C:4](Cl)[N:3]=1>C(O)C.C1CCCCC=1.[Pd]>[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:11][CH2:12][CH:13]([CH2:18][OH:17])[CH2:14][OH:15])=[CH:4][N:3]=1

참가 물질

5

반응물 1

HCID 117713466-Chloro-9-[2-(2,2-dimethyl-1,3-dioxan-5-yl)ethyl]-9H-purin-2-amine

생성물 1

HCID 1285176-Deoxypenciclovir수율 36.1%

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 702Ethanol용매HCID 8079Cyclohexene용매

실험 절차

To a solution of 2-amino-6-chloro-9-[2-(2,2-dimethyl-1,3-dioxan-5-yl)ethyl]purine (0.54 g, 1.75 mmol) in ethanol (10 ml) and cyclohexene (20 ml) was added 10% palladium-on-charcoal (400 mg) and the solution was refluxed for 7 hours. A further quantity of catalyst (200 mg) was added and the solution was refluxed overnight. The solution was filtered and washed through with methanol. To the filtrate was added hydrochloric acid (5M, 0.3 ml) and water (0.7 ml) and the solution was stirred for 30 minutes at room temperature. The solution was neutralised by addition of aqueous sodium bicarbonate and the solvent was removed. The residue was purified by column chromatography on silica gel eluting with chloroform-methanol (5:1, 4:1) to afford 2-amino-9-(4-hydroxy-3-hydroxymethylbut-1-yl)purine as a crystalline solid (150 mg, 36%), m.p. 156°-158° C.; λmax (H2O) 242 and 303 nm; λmax (KBr) 3320, 3210, 1640, 1610, 1580, and 1430 cm-1 ; δH [(CD3)2SO] 1.47 (1H, m, 3'-H), 1.78 (2H, q, J 7.2 Hz, 2'-H), 3.3-3.5 (4H, m, 2×4'-H), 4.12 (2H, t, J 7.4 Hz, 1'-H), 4.42 (2H, t, J 5.2 Hz, D2O exchangeable, 2×OH), 6.45 (2H, s, D2O exchangeable, 2-NH2), 8.06 (1H, s, 8-H), and 8.56 (1H, s, 6-H); (Found: C, 50.61; H, 6.45; N, 29.62%. C10H15N5O2 requires: C, 50.62; H, 6.37; N, 29.52%).

후처리

  1. temperaturethe solution was refluxed for 7 hours
  2. temperaturethe solution was refluxed overnight
  3. filtrationThe solution was filtered
  4. washwashed through with methanol
  5. additionTo the filtrate was added hydrochloric acid (5M, 0.3 ml) and water (0.7 ml)
  6. additionThe solution was neutralised by addition of aqueous sodium bicarbonate
  7. customthe solvent was removed
  8. customThe residue was purified by column chromatography on silica gel eluting with chloroform-methanol (5:1, 4:1)

출처 및 근거

ORD 기록
ord-4434c0d771104b01912a94f6390283bd
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05246937

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