Water → HCID 22861872, compound

HRID 976948Notes

Reaction equation

HRID 976948 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[N:7][C:8]([CH3:13])=[C:9]([CH3:12])[N:10]=2)[N:5]([C@@H:14]2[O:19][C@H:18]([CH2:20][OH:21])[C@@H:16]([OH:17])[CH2:15]2)[C:4](=[O:22])[N:3]=1.[Cl-].C[N+]1C=CN([C:30]([O:32][CH2:33][CH2:34][C:35]2[CH:40]=[CH:39][C:38]([N+:41]([O-:43])=[O:42])=[CH:37][CH:36]=2)=[O:31])C=1.O>CN(C=O)C>[CH3:12][C:9]1[N:10]=[C:11]2[C:6](=[N:7][C:8]=1[CH3:13])[N:5]([C@@H:14]1[O:19][C@H:18]([CH2:20][OH:21])[C@@H:16]([OH:17])[CH2:15]1)[C:4](=[O:22])[N:3]=[C:2]2[NH:1][C:30]([O:32][CH2:33][CH2:34][C:35]1[CH:40]=[CH:39][C:38]([N+:41]([O-:43])=[O:42])=[CH:37][CH:36]=1)=[O:31]

Participants

5

Reactant 3

HCID 962WaterHCID 13830215HCID 13830215, compoundHCID 54332664HCID 54332664, compound

Product 1

HCID 22861872HCID 22861872, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1.54 g (5 mmol) of 4-amino-6,7-dimethyl-1-(2-deoxy-β-D-ribofuranosyl)-pteridine-2-one (56) and 1.87 g (6 mmol) of 1-methyl-3-[2(4-nitrophenyl)ethoxycarbonyl]imidazolium chloride (see Himmelsbach, et al. Tetrahedron 40: 59 (1984) which is herein incorporated by reference) in 80 mL of anhydrous DMF was stirred at room temperature over night. To this solution was slowly added 100 mL of H2O with stirring. The solution was then cooled and the precipitate collected by suction and, after washing with methanol and ether and drying in a desiccator, gave 57 as 2.0 g (80% yield) of crude material. Recrystallization from methanol yielded 1.5 g (60% yield) of colorless crystals (m.p. 154°-155° C.).

Workup

  1. stirringwith stirring
  2. temperatureThe solution was then cooled
  3. customthe precipitate collected by suction
  4. washafter washing with methanol and ether
  5. customdrying in a desiccator

Sources & evidence

ORD record
ord-c19bec895e3c4d51a63a724ccb5fcab0
Source dataset
uspto-grants-1997_03
Patent number
US05612468

Reaction notes

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