Pyridine → HCID 178476356, compound

HRID 1905362Notes

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].C([O:22][CH2:23][CH3:24])(=O)C.C(O[C:29](=[O:31])[CH3:30])(=O)C.N1C=CC=[CH:34][CH:33]=1.[O-:38][CH2:39][CH3:40].[Na+]>>[CH3:33][C:34]1[N:18]=[C:16]([OH:17])[C:3]2[N:4]=[CH:5][N:6]([C:2]=2[N:1]=1)[C@@H:7]1[O:13][C@H:12]([CH2:14][O:15][C:39](=[O:38])[CH3:40])[C@@:10]([C:29](=[O:31])[CH3:30])([OH:11])[C@@:8]1([C:23](=[O:22])[CH3:24])[OH:9]

Participants

Reactant 5

HCID 1049Pyridine

HCID 7918Acetic Anhydride

HCID 8857Ethyl Acetate

HCID 17513Acadesine

HCID 2723922Sodium ethoxide

Product 1

HCID 178476356HCID 178476356, compoundYield 95%

Conditions

Temperature: 120 °C

Procedure

6 g of 5-amino-1-β-D-ribofuranosyl-4-imidazolecarboxamide was dissolved in 250 ml of 1N sodium ethoxide. 20 ml of ethyl acetate was added thereto, and the reaction mixture was heated for 3 hours at 120° C. After the solution was neutralized and desalted, 70 ml of acetic anhydride and 70 ml of pyridine were added thereto and the solution was stirred for 12 hours at room temperature. The solvent was distilled off under reduced pressure to give 9 g of 2-methyl-2',3',5'-O-triacetylinosine (yield: 95%).

Workup

distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record: ord-3abe31c3f0d5462ca9685f463822b2a5
Source dataset: uspto-grants-1989_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04843066

Reaction notes

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