Ethanol → HCID 66906443, compound

HRID 1689653Notes

Reaction equation

HRID 1689653 reaction equation
[OH:1][C@H:2]1[C@H:6]2[O:7][CH2:8][C@:3]1([CH2:18][OH:19])[O:4][C@H:5]2[N:9]1[CH:17]=[C:15]([CH3:16])[C:13](=[O:14])[NH:12][C:10]1=[O:11].[C:20](OC(=O)C)(=[O:22])[CH3:21].[CH2:27]([OH:29])[CH3:28]>N1C=CC=CC=1.CN(C1C=CN=CC=1)C>[C:20]([O:1][C@H:2]1[C@H:6]2[O:7][CH2:8][C@@:3]1([CH2:18][O:19][C:27](=[O:29])[CH3:28])[O:4][C@H:5]2[N:9]1[CH:17]=[C:15]([CH3:16])[C:13](=[O:14])[NH:12][C:10]1=[O:11])(=[O:22])[CH3:21]

Participants

6

Reactant 3

HCID 702EthanolHCID 7918Acetic AnhydrideHCID 102210801-[2,5-Anhydro-4-C-(hydroxymethyl)-alpha-L-lyxofuranosyl]-5-methyl-2,4(1H,3H)-pyrimidinedione

Product 1

HCID 66906443HCID 66906443, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

To a stirred solution of nucleoside 37 (209.8 mg, 0.78 mmol) in anhydrous pyridine (2.5 cm3) was added acetic anhydride (0.3 cm3, 3.23 mmol) and a catalytic amount of DMAP (5 mg). After stiffing for 2 h, ethanol was added (4 cm3) and the mixture was evaporated under reduced pressure. The residue was redissolved in dichloromethane and washed with a saturated aqueous solution of sodium hydrogencarbonate (7 cm3). The organic phase was dried (Na2SO4), and evaporated under reduced pressure. The residue was purified by silica gel column chromatography using dichloromethane/methanol (97:3, v/v) as eluent affording 64 as a white solid material (249 mg, 90%). δC (CDCl3) 169.59, 163.20, 149.50, 133.55, 110.64, 87.05, 85.38, 77.84, 71.70, 71.02, 58.60, 20.62, 20.53, 12.78. FAB-MS m/z 355 [M+H]+.

Workup

  1. customthe mixture was evaporated under reduced pressure
  2. dissolutionThe residue was redissolved in dichloromethane
  3. washwashed with a saturated aqueous solution of sodium hydrogencarbonate (7 cm3)
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. customevaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-fd982a0a742f4ca5ad41e06cac47e3c4
Source dataset
uspto-grants-2012_04
Patent number
US08153365B2

Reaction notes

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