Pyridine → 9-((2R,3R,4S)-4-t-butyldimethylsiloxymethyl-3-hydroxymethyl-oxetan-2-yl)adenine

HRID 37391Notes

Reaction equation

HRID 37391 reaction equation
[OH:1][CH2:2][C@@H:3]1[C@@H:6]([CH2:7][OH:8])[O:5][C@H:4]1[N:9]1[CH:17]=[N:16][C:15]2[C:10]1=[N:11][CH:12]=[N:13][C:14]=2[NH2:18].N1C=CC=CC=1.[C:25]([Si:29](Cl)([CH3:31])[CH3:30])([CH3:28])([CH3:27])[CH3:26]>C(OCC)(=O)C>[O:8]([CH2:7][C@H:6]1[O:5][C@@H:4]([N:9]2[CH:17]=[N:16][C:15]3[C:10]2=[N:11][CH:12]=[N:13][C:14]=3[NH2:18])[C@@H:3]1[CH2:2][OH:1])[Si:29]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:31])[CH3:30]

Participants

5

Reactant 3

HCID 1049PyridineHCID 28928tert-Butyldimethylsilyl chlorideHCID 72214Oxetanocin

Product 1

HCID 141922579-((2R,3R,4S)-4-t-butyldimethylsiloxymethyl-3-hydroxymethyl-oxetan-2-yl)adenine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

In a round-bottom flask were placed 10 g of 9-((2R, 3R, 4S)-3,4-bis-hyroxymethyl-oxetan-2-yl)-adenine and 100 mL of pyridine. To the system was added 6.4 g of tert-butylchlorodimethylsilane, and the reaction mixture was stirred under nitrogen at room temperature for 1 day. The mixture was diluted with ethyl acetate and washed with saturated aqueous sodium bicarbonate and brine, dried (sodium sulfate) and concentrated with a rotary evaporator. The residue was purified by column chromatography to afford 9-((2R,3R,4S)-4-t-butyldimethylsiloxymethyl-3-hydroxymethyl-oxetan-2-yl)adenine.

Workup

  1. customIn a round-bottom flask were placed
  2. washwashed with saturated aqueous sodium bicarbonate and brine
  3. dry with materialdried (sodium sulfate)
  4. concentrationconcentrated with a rotary evaporator
  5. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-8ac12c5947d84032af11f14307246012
Source dataset
uspto-grants-1995_05
Patent number
US05420276

Reaction notes

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