Diazomethane → 5-amino-1-(2-O-methyl-beta-D-ribofuranosyl)imidazole-4-carboxamide

HRID 1955953Notes

Reaction equation

HRID 1955953 reaction equation
[NH2:1][C:2]1[N:6]([C@@H:7]2[O:13][C@H:12]([CH2:14][OH:15])[C@@H:10]([OH:11])[C@H:8]2[OH:9])[CH:5]=[N:4][C:3]=1[C:16]([NH2:18])=[O:17].[N+](=[CH2:21])=[N-].O.O.[Sn](Cl)Cl>CN(C)C=O.CO.CCOCC>[NH2:1][C:2]1[N:6]([C@@H:7]2[O:13][C@H:12]([CH2:14][OH:15])[C@@H:10]([OH:11])[C@H:8]2[O:9][CH3:21])[CH:5]=[N:4][C:3]=1[C:16]([NH2:18])=[O:17]

Participants

7

Reactant 3

HCID 9550DiazomethaneHCID 17513AcadesineHCID 61436Stannous chloride dihydrate

Product 1

HCID 543675615-amino-1-(2-O-methyl-beta-D-ribofuranosyl)imidazole-4-carboxamide

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

5-Amino-1-β-D-ribofuranosylimidazole-4-carboxamide (5.2 g, 20 mmol) was dissolved in 40 ml hot dimethylformamide and diluted with 70 ml methanol containing 35 mg tin(II) chloride dihydrate. A solution of 0.1 mol of diazomethane in 200 ml of ether was added in portions over 45 min. After each addition, 20 mg of tin(II) chloride dihydrate was added. The resulting mixture was filtered and evaporated to give a syrup. The syrup was dissolved in 25 ml of methanol and upon cooling yielded crystalline 5-amino-1-(2-O-methyl-β-D-ribofuranosyl)imidazole-4-carboxamide which was collected by filtration and dried. Yield was 1.2 g, melting point 114°-117° C.

Workup

  1. additionwas added
  2. filtrationThe resulting mixture was filtered
  3. customevaporated
  4. customto give a syrup
  5. temperatureupon cooling

Sources & evidence

ORD record
ord-dd63d851e63c4e4bbeb48683d98934cd
Source dataset
uspto-grants-1998_07
Patent number
US05777100

Reaction notes

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