HCID 10863302, compound → 1-[2,5-Anhydro-4-C-(hydroxymethyl)-alpha-L-lyxofuranosyl]-5-methyl-2,4(1H,3H)-pyrimidinedione

HRID 1663530Notes

Reaction equation

HRID 1663530 reaction equation
C([O:8][C@H:9]1[C@H:13]2[O:14][CH2:15][C@:10]1([CH2:25][O:26]CC1C=CC=CC=1)[O:11][C@H:12]2[N:16]1[CH:24]=[C:22]([CH3:23])[C:20](=[O:21])[NH:19][C:17]1=[O:18])C1C=CC=CC=1>C(O)C.[OH-].[Pd+2].[OH-]>[OH:8][C@H:9]1[C@H:13]2[O:14][CH2:15][C@:10]1([CH2:25][OH:26])[O:11][C@H:12]2[N:16]1[CH:24]=[C:22]([CH3:23])[C:20](=[O:21])[NH:19][C:17]1=[O:18]

Participants

4

Reactant 1

HCID 10863302HCID 10863302, compound

Product 1

HCID 102210801-[2,5-Anhydro-4-C-(hydroxymethyl)-alpha-L-lyxofuranosyl]-5-methyl-2,4(1H,3H)-pyrimidinedione

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

A solution of nucleoside 36 (97 mg, 0.215 mmol) in ethanol (1.5 cm3) was stirred at room temperature and 20% palladium hydroxide over carbon (50 mg) was added. The mixture was degassed several times with argon and placed in a hydrogen atmosphere with a balloon. After stirring for 4 h, the mixture was purified by silica gel column chromatography using dichloromethane-methanol (97:3, v/v) as eluent to give nucleoside 37 as a white solid material (57 mg, 98%). δH ((CD3)2SO) 11.33 (1H, br s, NH), 7.62 (1H, d, J 1.1 Hz, 6-H), 5.65 (1H, d, J 4.4 Hz, 3′-OH), 5.41 (1H, s, 1′-H), 5.19 (1H, t, J 5.6 Hz, 5′-OH), 4.11 (1H, s, 2′-H), 3.91 (1H, d, J 4.2 Hz, 3′-H), 3.82 (1H, d, J 7.7 Hz, 1″-Ha), 3.73 (1H, s, H′-5a), 3.76 (1H, s, 5′-Hb), 3.63 (1H, d, J 7.7 Hz, 1″-Hb), 1.78 (3H, d, J 0.7 Hz, CH3). δC (CDCl3) 166.7 (C-4), 152.1 (C-2), 137.0 (C-6), 110.9 (C-5), 90.5, 88.4 (C-1′, C-4′), 80.9, 72.5, 70.4 (C-2′, C-3′, C-5′), 57.7 (C-1″), 12.6 (CH3). EI-MS m/z 270 [M]+.

Workup

  1. customThe mixture was degassed several times with argon
  2. customthe mixture was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-0885d69dab98450a93d7463671f3cd9d
Source dataset
uspto-grants-2011_10
Patent number
US08034909B2

Reaction notes

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