Adenine → HCID 15858375, compound

HRID 442701Notes

Reaction equation

HRID 442701 reaction equation
[N:1]1[C:9]([NH2:10])=[C:8]2[C:4]([N:5]=[CH:6][NH:7]2)=[N:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].[O:17]1[CH:19]([CH2:20][S:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[CH2:18]1.C(Cl)(Cl)Cl.CO>CN(C)C=O>[OH:17][CH:19]([CH2:20][S:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[CH2:18][N:5]1[CH:6]=[N:7][C:8]2[C:4]1=[N:3][CH:2]=[N:1][C:9]=2[NH2:10]

Participants

6

Reactant 4

HCID 190AdenineHCID 11430Potassium CarbonateHCID 13417926HCID 13417926, compoundHCID 21584188Chloroform methanol

Product 1

HCID 15858375HCID 15858375, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of adenine (0.829 g, 6.10 mmol), anhydrous potassium carbonate (45 mg) and rac-1,2-epoxy-3-octadecylthiopropane (2.0 g, 5.83 mmol) in anhydrous dimethyl formamide (10 mL) is stirred at 70°-75° C. for 20 hours under a nitrogen atmosphere. The reaction mixture is filtered directly without cooling and the filtrate is concentrated under reduced pressure to afford a white residue. The residue is stirred with 95:5 (v/v) chloroform-methanol. The insoluble solid is filtered, purified by chromatography, and dried in vacuo to 9-[2'-hydroxy-3'-octadecylthiopropyl]-adenine.

Workup

  1. filtrationThe reaction mixture is filtered directly
  2. temperaturewithout cooling
  3. concentrationthe filtrate is concentrated under reduced pressure
  4. customto afford a white residue
  5. filtrationThe insoluble solid is filtered
  6. custompurified by chromatography
  7. dry with materialdried in vacuo to 9-[2'-hydroxy-3'-octadecylthiopropyl]-adenine

Sources & evidence

ORD record
ord-968aa61dd1b34789b6bdc6cf7c378127
Source dataset
uspto-grants-1999_04
Patent number
US05891881

Reaction notes

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