Hydrochloric Acid → HCID 135499550, compound

HRID 263395Notes

Reaction equation

HRID 263395 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:11][CH2:12][CH2:13][CH2:14][B:15]([OH:17])[OH:16])=[C:4](Cl)[N:3]=1.Cl.[OH-:20].[Na+]>>[OH:16][B:15]([OH:17])[CH2:14][CH2:13][CH2:12][CH2:11][N:8]1[CH:7]=[N:6][C:5]2[C:4](=[O:20])[NH:3][C:2]([NH2:1])=[N:10][C:9]1=2

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 461300HCID 461300, compound2×

Product 1

HCID 135499550HCID 135499550, compoundYield 81%

Procedure

The compound prepared in Example 3, 2-amino-6-chloro-9-(4-dihydroxyborylbutyl)purine, (0.5 g, 1.85 mmol) was added to aqueous HCl (5 mL, 2N), and the reaction mixture was heated to reflux for 5 hours. After cooling to room temperature, aqueous NaOH (10%) was added to neutralize the reaction mixture to pH 7. Water was evaporated under high vacuum, and methanol was added to the residue to remove the unreacted starting material. The remaining solid was washed with water (3×20 mL), then stirred in water overnight. After filtration, the product was air-dried for 2 days. Yield 81%; Wt. 0.38 g; mp 202°-205° C.; 1H NMR (DMSO-d6) 0.55-0.68 (t, B CH2), 1.20-1.32 (m, B CH2 CH2), 1.62-1.75 (m, B CH2 CH2 CH2), 3.88-3.98 (t, CH2 CH2 N), 6.33-6.50 (s, H2N C2 guanine), 7.40-7.45 (s, (HO)2 B), 7.68-7.71 (s, H C8 guanine), 10.47-10.53 (H N3 guanine). Electrospray Mass Spectrum (MH)+ (low resolution); Calcd. 252.12 (C9H14O3N5B); Found 252.10 (79 ppm).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 5 hours
  3. customWater was evaporated under high vacuum, and methanol
  4. additionwas added to the residue
  5. customto remove the
  6. washThe remaining solid was washed with water (3×20 mL)
  7. filtrationAfter filtration
  8. customthe product was air-dried for 2 days

Sources & evidence

ORD record
ord-37bed35b9aaf4e6196616455089a8d0e
Source dataset
uspto-grants-1997_07
Patent number
US05643893

Reaction notes

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