Hydrazine → HCID 10240087, compound

HRID 1862010Notes

Reaction equation

HRID 1862010 reaction equation
C1(=O)[N:5]([CH2:6][CH2:7][O:8][C@@H:9]2[C@H:13]([OH:14])[C@@H:12]([CH2:15][O:16][C:17]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)([C:26]3[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=3)[C:18]3[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=3)[O:11][C@H:10]2[N:40]2[CH:47]=[C:46]([CH3:48])[C:44](=[O:45])[NH:43][C:41]2=[O:42])C(=O)C2=CC=CC=C12.NN>CO>[CH3:7][OH:8].[OH-:8].[NH4+:5].[NH2:5][CH2:6][CH2:7][O:8][C@@H:9]1[C@H:13]([OH:14])[C@@H:12]([CH2:15][O:16][C:17]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)([C:18]2[CH:19]=[CH:20][C:21]([O:24][CH3:25])=[CH:22][CH:23]=2)[C:26]2[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=2)[O:11][C@H:10]1[N:40]1[CH:47]=[C:46]([CH3:48])[C:44](=[O:45])[NH:43][C:41]1=[O:42]

Participants

5

Reactant 2

HCID 9321HydrazineHCID 10628754HCID 10628754, compound

Product 2

HCID 10240087HCID 10240087, compoundYield 212.5%HCID 21894508Ammonium hydroxide methanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2′-O-Phthalimidoethyl-5′-O-DMT-5-methyluridine (3, 21.1 g, 0.029 mol) was dissolved in methanol (500 mL). Anhydrous hydrazine (4.9 mL, 0.15 mol) was added and the solution was heated to reflux. TLC after 3 h indicated a complete reaction. The residue was purified by chromatography on silica gel using methanol and then methanol-ammonium hydroxide (98:2) to give 4 (12.4 g, 70%). The material was completely soluble in methylene chloride and traces of silica from leaching of the column were removed by filtration at this stage and reevaporating the solution.

Workup

  1. temperaturethe solution was heated to reflux
  2. customa complete reaction
  3. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-dad4269e502448afb440b7d019eabc62
Source dataset
uspto-grants-2003_03
Patent number
US06534639B1

Reaction notes

Loading…