Hydrochloric Acid → 9-(3,4-dihydroxybutyl)guanine

HRID 2412867Notes

Reaction equation

HRID 2412867 reaction equation
C([O:3][C:4](=O)[CH:5]([OH:19])[CH2:6][CH2:7][N:8]1[CH:16]=[N:15][C:14]2[C:13](=[O:17])[NH:12][C:11]([NH2:18])=[N:10][C:9]1=2)C.[BH4-].[Na+].Cl>C(O)(C)C>[OH:19][CH:5]([CH2:4][OH:3])[CH2:6][CH2:7][N:8]1[CH:16]=[N:15][C:14]2[C:13](=[O:17])[NH:12][C:11]([NH2:18])=[N:10][C:9]1=2

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 4311764Sodium borohydrideHCID 135797562HCID 135797562, compound

Product 1

HCID 1354156129-(3,4-dihydroxybutyl)guanine

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a suspension of ethyl 4-(2-amino-1,6-dihydro-6-oxopurin-9-yl)-2-hydroxybutyrate (prepared according to Example 4) in iso-propanol was added an excess of sodium borohydride and the mixture was refluxed over night (at least 8 hours). Hydrochloric acid was added until a clear solution was obtained (neutral pH). After removal of the solvent the residue was dissolved in a minimum amount of boiling water and kept at 0° C. for a couple of hours. The solid was filtered off. The filtrate was evaporated at reduced pressure and the residue dissolved in hydrochloric acid (1 mol/l) and adsorbed on a cation exchange resin (Dowex 50 W, H+ -form). The resin was washed with water and then eluted with 5% ammonium hydroxide. The eluent was evaporated to give a crystalline solid which was recrystallized from water to afford colourless needles. M.p. 260°-1° C. (dec.) (uncorrected) UV spectra (hydrochloric acid 0.01 mol/l): λmax (nm) 277, 253 (ε=11500) M.S: 11.2 a J. (int): 239 (M+, 0.13), 222 (0.19), 221 (0.11), 152 (0.43), 151 (0.56), 44 (1.0).

Workup

  1. temperaturethe mixture was refluxed over night (at least 8 hours)
  2. customwas obtained (neutral pH)
  3. customAfter removal of the solvent the residue
  4. dissolutionwas dissolved in a minimum amount of boiling water
  5. waitkept at 0° C. for a couple of hours
  6. filtrationThe solid was filtered off
  7. customThe filtrate was evaporated at reduced pressure
  8. dissolutionthe residue dissolved in hydrochloric acid (1 mol/l)
  9. washThe resin was washed with water
  10. washeluted with 5% ammonium hydroxide
  11. customThe eluent was evaporated
  12. customto give a crystalline solid which
  13. customwas recrystallized from water
  14. customto afford colourless needles

Sources & evidence

ORD record
ord-47c24049f86044668b549d31aaf7c111
Source dataset
uspto-grants-1985_01
Patent number
US04495190

Reaction notes

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