Ethanol → HCID 11056798, compound

HRID 1086145Notes

Reaction equation

HRID 1086145 reaction equation
[C:1]([C:3]1[C:4](=[O:18])[NH:5][C:6](=[O:17])[N:7]([CH:16]=1)[C@@H:8]1[O:15][C@H:12]([CH2:13][OH:14])[C@@H:10]([OH:11])[CH2:9]1)#[CH:2].N1C=CC=CC=1.[C:25](OC(=O)C)(=[O:27])[CH3:26].[CH2:32]([OH:34])[CH3:33]>>[C:25]([O:11][C@@H:10]1[C@@H:12]([CH2:13][O:14][C:32](=[O:34])[CH3:33])[O:15][C@@H:8]([N:7]2[CH:16]=[C:3]([C:1]#[CH:2])[C:4](=[O:18])[NH:5][C:6]2=[O:17])[CH2:9]1)(=[O:27])[CH3:26]

Participants

5

Reactant 4

HCID 702EthanolHCID 1049PyridineHCID 7918Acetic AnhydrideHCID 4721725-Ethynyl-2′-deoxyuridine

Product 1

HCID 11056798HCID 11056798, compoundYield 92%

Procedure

5-ethynyl-2'-deoxyuridine (J. Med. Chem., 26(5), 661-6, (1983)) (1.26 g, 5.0 mmole), 10 ml of dry pyridine, and 1.22 g of acetic anhydride (12.0 mmole) were stirred together at room temperature for 20 hr. The resulting clear solution was evaporated to give a syrupy residue which upon co-evaporation with ethanol gave a white solid. Re-crystallisation from ethanol gave 1.49 g (92%) of the title compound as white crystals melting at 152°-4° C.

Workup

  1. customThe resulting clear solution was evaporated
  2. customto give a syrupy residue which upon co-evaporation with ethanol
  3. customgave a white solid

Sources & evidence

ORD record
ord-c43e914791474864bfade9b741e91fe8
Source dataset
uspto-grants-1991_07
Patent number
US05028596

Reaction notes

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