Acetonitrile → 2-Methyladenosine

HRID 1905363Notes

Reaction equation

HRID 1905363 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]#[N:17].[C:18](#[N:20])[CH3:19]>CO.N>[CH3:19][C:18]1[N:20]=[C:16]([NH2:17])[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][OH:15])[C@@H:10]([OH:11])[C@H:8]1[OH:9]

Participants

4

Reactant 2

HCID 6342AcetonitrileHCID 109775505-amino-1-beta-D-ribofuranosyl-4-cyanoimidazole

Product 1

HCID 4598902-MethyladenosineYield 35.9%

Reagents, catalysts & solvents 1

HCID 21705897Ammonia methanolSolvent

Conditions

Temperature
180 °C

Procedure

10 g of 5-amino-1-β-D-ribofuranosyl-4-imidazolecarbonitrile was dissolved in 20% ammonia methanol solution. 10 ml of acetonitrile was added thereto and the solution was heated for 5 hours at 180° C. The solvent was distilled off, purified by silica gel column chromatography and recrystallized from methanol to give 4.2 g of 2-methyladenosine (yield: 35.9%). 2-methyladenosine was methylated in the same manner as the above-mentioned [METHOD 1] to give Compound 5 and Compound 6.

Workup

  1. distillationThe solvent was distilled off
  2. custompurified by silica gel column chromatography
  3. customrecrystallized from methanol

Sources & evidence

ORD record
ord-ad34449c2e004f64811a41dcface1a3e
Source dataset
uspto-grants-1989_06
Patent number
US04843066

Reaction notes

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