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

HRID 5865

反応式

HRID 5865 の反応式
[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

参加物

5

反応物 1

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

生成物 1

HCID 1285176-Deoxypenciclovir収率 36.1%

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 702Ethanol溶媒HCID 8079Cyclohexene溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-4434c0d771104b01912a94f6390283bd
出典データセット
uspto-grants-1993_09
特許番号
US05246937

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