Dimethylformamide → Guanine

HRID 2412869Notes

Reaction equation

HRID 2412869 reaction equation
[CH:1]1[NH:2][C:3]2[N:9]=[C:8]([NH2:10])[N:7]=[C:6](Cl)[C:4]=2[N:5]=1.[H-].[Na+].CN(C)C=[O:17]>>[NH:7]1[C:6](=[O:17])[C:4]2[NH:5][CH:1]=[N:2][C:3]=2[N:9]=[C:8]1[NH2:10]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 1785084356-chloro-1H-purin-2-amine

Product 1

HCID 135398634Guanine

Conditions

Temperature
100 °C

Procedure

6-Chloroguanine (0.75 g) and sodium hydride (60% in oil, 0.18 g) in dry dimethylformamide were stirred at room temperature for one hour. DL-erythro-2,2-Dimethyl-4-p-toluenesulfonyloxymethyl-5-hydroxymethyl-1,3-dioxolane [0.70 g, prepared according to A. Holy, Coll. Czech. Chem. Commun Vol 44, pages 593-612 (1979)] was added and the reaction mixture was heated at 100° C. for 17 hours, after which it was filtered through a Celite pad, and the solution was evaporated in vacuo. The residue was refluxed with acetic acid (25 ml) for 2 hours. The solvent was evaporated and the residue was coevaporated with water (3×5 ml). The residue was dissolved in a small volume of 1N hydrochloric acid, and added to a column of Dowex 50×8 (H+, 70 ml)which was eluted with water (1 liter) followed by aqueous ammonia (diluted 1/10). The elution was monitored by a UV detector. The appropriate fractions were evaporated in vacuo, and the residue was coevaporated with water several times, finally dissolved in boiling water (230 ml) and filtered to give 9-(DL-erythro-2,3,4-trihydroxybutyl) guanine (0.20 g). NMR (DMSO-d6)δ: 7,8 (s,8C-H); 6.4 (NH2); 4.22 (N-CH2).

Workup

  1. additionCommun Vol 44, pages 593-612 (1979)] was added
  2. filtrationafter which it was filtered through a Celite pad
  3. customthe solution was evaporated in vacuo
  4. temperatureThe residue was refluxed with acetic acid (25 ml) for 2 hours
  5. customThe solvent was evaporated
  6. dissolutionThe residue was dissolved in a small volume of 1N hydrochloric acid
  7. additionadded to a column of Dowex 50×8 (H+, 70 ml)which
  8. washwas eluted with water (1 liter)
  9. washThe elution
  10. customThe appropriate fractions were evaporated in vacuo
  11. dissolutionfinally dissolved
  12. filtrationfiltered

Sources & evidence

ORD record
ord-9f6473d4396746f7b41d3d0ac23e55f9
Source dataset
uspto-grants-1985_01
Patent number
US04495190

Reaction notes

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