Trifluoroacetic acid → 9-(4-Hydroxy-3-hydroxymethyl-2-butenyl)guanine

HRID 2291853Notes

Reaction equation

HRID 2291853 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:11][CH:12]=[C:13]([CH2:23][O:24]CC2C=CC=CC=2)[CH2:14][O:15]CC2C=CC=CC=2)=[C:4](Cl)[N:3]=1.FC(F)(F)C(O)=[O:36]>O>[OH:15][CH2:14][C:13]([CH2:23][OH:24])=[CH:12][CH2:11][N:8]1[CH:7]=[N:6][C:5]2[C:4](=[O:36])[NH:3][C:2]([NH2:1])=[N:10][C:9]1=2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 21278111HCID 21278111, compound

Product 1

HCID 1354253129-(4-Hydroxy-3-hydroxymethyl-2-butenyl)guanineYield 41%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of 4-(2-amino-6-chloropurin-9-yl)-1-benzyloxy-2-benzyloxymethyl-2-butene (148 mg, 0.329 mmol), 1.8 ml of trifluoroacetic acid and 0.2 ml of water in a sealed ampoule was kept at 110° C. for 17 h. After cooling the mixture was diluted with 2 ml of water, heated to boiling for one minute, and evaporated to dryness in vacuum, dissolved in water and re-evaporated. Chromatography (silica gel, ethyl acetate+methanol+water 70+20+10 parts of volume) afforded 34 mg (41%) of 9-[4-hydroxy-3-(hydroxymethyl)-2-butenyl]guanine.

Workup

  1. temperatureAfter cooling the mixture
  2. temperatureheated
  3. customevaporated to dryness in vacuum
  4. dissolutiondissolved in water
  5. customre-evaporated

Sources & evidence

ORD record
ord-b4b18546f0bf4f429b68e91ec7f8e05c
Source dataset
uspto-grants-1989_01
Patent number
US04798833

Reaction notes

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