Hydrochloric Acid → HCID 13869775, compound

HRID 1461524Notes

Reaction equation

HRID 1461524 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][CH:13]2[CH2:18][O:17]C(C)(C)[O:15][CH2:14]2)=[C:4](Cl)[N:3]=1.[CH3:22][CH:23]([CH3:25])[O-:24].[Na+].Cl.C(=O)(O)[O-].[Na+]>C(O)(C)C.O>[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:11][CH2:12][CH:13]([CH2:14][OH:15])[CH2:18][OH:17])=[C:4]([O:24][CH:23]([CH3:25])[CH3:22])[N:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 109204432-Propanol, sodium salt (1:1)HCID 117713466-Chloro-9-[2-(2,2-dimethyl-1,3-dioxan-5-yl)ethyl]-9H-purin-2-amine

Product 1

HCID 13869775HCID 13869775, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

A solution of 2-amino-6-chloro-9-[2-(2,2-dimethyl-1,3-dioxan-5-yl)ethyl]purine (0.25 g, 0.8 mmol) in isopropanol (2.5 ml) containing sodium isopropoxide 0.5 M) was stirred at 60° for 25 minutes. After cooling, hydrochloric acid (5 M, 0.3 ml) and water (0.7 ml) were added and the solution was stirred for 15 minutes at room temperature. The solution was neutralised by addition of aqueous sodium bicarbonate and the solvent was removed. The residue was extracted with chloroform-ethanol (2:1) and the solution purified by column chromatography on silica gel eluting with chloroform-methanol (7:1) to afford 2-amino-9-(4-hydroxy-3-hydroxymethylbut-1-yl)-6-isopropoxypurine which was crystallised from chloroformcarbon tetrachloride (0.18 g, 76%), m.p. 111.5°-113.5° C.; δH [(CD3)2SO] 1.34 (6 H, d, J 6.3 Hz, C(CH3)2), 1.45 (1H, m, 3' -H), 1.74 (2 H, q, J 7.2 Hz, 2'-H), 3.3-3.5 (4 H, AB part of ABX, 2×4'-H), 4.06 (2 H, t, J 7.3 Hz, 1'-H), 4.40 (2 H, br, 2×OH), 5.49 (1 H, septet, J 6.3 Hz, CH(CH3)2), 6.27 (2 H, s, 2-NH2), and 7.83 (1 H, s, 8 -H).

Workup

  1. temperatureAfter cooling
  2. stirringthe solution was stirred for 15 minutes at room temperature
  3. customthe solvent was removed
  4. extractionThe residue was extracted with chloroform-ethanol (2:1)
  5. customthe solution purified by column chromatography on silica gel eluting with chloroform-methanol (7:1)

Sources & evidence

ORD record
ord-90d586145c1a4d74b00db6b5e4cdcd50
Source dataset
uspto-grants-1991_12
Patent number
US05075445

Reaction notes

Loading…