Adenine → HCID 178508642, compound

HRID 2380572Notes

Reaction equation

HRID 2380572 reaction equation
CC1C=CC(S(O[CH:12]2[CH2:15][CH:14]([CH2:16][OH:17])[CH2:13]2)(=O)=O)=CC=1.[N:18]1[C:26]([NH2:27])=[C:25]2[C:21]([N:22]=[CH:23][NH:24]2)=[N:20][CH:19]=1.C1OCCOCCOCCOCCOCCOC1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[NH2:27][C:26]1[N:18]=[CH:19][N:20]=[C:21]2[C:25]=1[N:24]=[CH:23][N:22]2[C@@H:12]1[CH2:13][C@H:14]([CH2:16][OH:17])[CH2:15]1

Participants

6

Reactant 4

HCID 190AdenineHCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 18954691cis-3-(Hydroxymethyl)cyclobutyl Tosylate

Product 1

HCID 178508642HCID 178508642, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 720 mg (2.0 mmol) of 3[[(4-methylphenyl)sulfonyl]oxy]cyclobutanemethanol, benzoate ester (95% trans isomer and 5% cis isomer) in 20 ml of dry dimethylformamide under nitrogen was added adenine (405 mg, 3 mmol), 18-crown-6 (528 mg, 2 mmol), and potassium carbonate (414 mg, 3 mmol). The mixture was stirred at 110° for 18 hours and then concentrated in vacuo to a residue. Water was added and the suspension was adjusted to pH 7.0 using 1N hydrochloric acid. Removal of solvent in vacuo gave a residue, which was chromatographed over 200 ml of LPS-1 silica gel using 4% methanol in dichloromethane to give 430 mg of desired product as a white solid.

Workup

  1. concentrationconcentrated in vacuo to a residue
  2. additionWater was added
  3. customRemoval of solvent in vacuo
  4. customgave a residue, which
  5. customwas chromatographed over 200 ml of LPS-1 silica gel using 4% methanol in dichloromethane

Sources & evidence

ORD record
ord-969e11c47b8c473e94ae141f12c52092
Source dataset
uspto-grants-1994_11
Patent number
US05369098

Reaction notes

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