Methyl iodide → HCID 9926647, compound

HRID 1905365Notes

Reaction equation

HRID 1905365 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([NH2:21])[C:5]2[N:6]=[CH:7][N:8]([C:19]=2[N:20]=1)[C@@H:9]1[O:18][C@H:15]([CH2:16][OH:17])[C@@H:13]([OH:14])[C@H:10]1[O:11][CH3:12].[CH3:22]I>CN(C)C=O>[CH3:1][C:2]1[N:3]=[C:4]([NH:21][CH3:22])[C:5]2[N:6]=[CH:7][N:8]([C:19]=2[N:20]=1)[C@@H:9]1[O:18][C@H:15]([CH2:16][OH:17])[C@@H:13]([OH:14])[C@H:10]1[O:11][CH3:12]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 67644571HCID 67644571, compound2×

Product 1

HCID 9926647HCID 9926647, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

1 g of 2,2'-O-dimethyladenosine (Compound 5) was dissolved in 5 ml of dimethylformamide, and 2 ml of methyl iodide was added thereto and the solution was stirred for 30 to 40 minutes. After the solvent was distilled off, 5 ml of 0.5N sodium hydroxide was added and the solution was heated for 75 minutes at 100° C. The solution was neutralized and desalted by hydrophobic column chromatography, and then recrystallized from methanol to give 2,N6,2'-O-trimethyladenosine (Compound 21).

Workup

  1. distillationAfter the solvent was distilled off
  2. addition5 ml of 0.5N sodium hydroxide was added
  3. customrecrystallized from methanol

Sources & evidence

ORD record
ord-35e2b87c2fe743ad8f5a018020a0319f
Source dataset
uspto-grants-1989_06
Patent number
US04843066

Reaction notes

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