Hydrochloric Acid → HCID 13869777, compound

HRID 1370009Notes

Reaction equation

HRID 1370009 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[H][H].[NH2:12][C:13]1[N:21]=[C:20]2[C:16]([N:17]=[CH:18][N:19]2[CH2:22][CH2:23][CH:24]2[CH2:29][O:28]C(C)(C)[O:26][CH2:25]2)=[C:15](Cl)[N:14]=1.Cl.C(=O)(O)[O-].[Na+]>O1CCOCC1.O>[NH2:12][C:13]1[N:21]=[C:20]2[C:16]([N:17]=[CH:18][N:19]2[CH2:22][CH2:23][CH:24]([CH2:29][OH:28])[CH2:25][OH:26])=[C:15]([O:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[N:14]=1

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 996PhenolHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 117713466-Chloro-9-[2-(2,2-dimethyl-1,3-dioxan-5-yl)ethyl]-9H-purin-2-amineHCID 178418361HCID 178418361, compound

Product 1

HCID 13869777HCID 13869777, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of phenol (113 mg, 1.2 mmol) in dry dioxan (2.5 ml) was added sodium hydride (60% dispersion in oil; 48 mg, 1.2 mmol). After evolution of hydrogen ceased, 2-amino-6-chloro-9-[2-(2,2-dimethyl-1,3-dioxan-5-yl)ethyl]purine (0.25 g, 0.8 mmol) was added and the mixture was stirred at 75° for 3.5 hours. After cooling, water (0.8 ml) and hydrochloric acid (5M, 0.2 ml) were added and the solution was stirred for 30 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 (9:1) to afford 2-amino-9-(4-hydroxy-3-hydroxymethylbut-1-yl)-6-phenoxypurine (145 mg, 55%), m.p. 173-175° C.; δH [(CD3)2SO] 1.48 (1H, m, 3′-H), 1.78 (2H, q, J 7.1 Hz, 2′-H), 3.3-3.5 (4H, m, 2×4′-H), 4.12 (2H, t, J 7.4 Hz, 1′-H), 4.42 (2H, t, J 5.1 Hz, D2O exchangeable, 2×OH), 6.35 (2H, s, D2O exchangeable, 2-NH2), 7.2-7.5 (5H, m, C6H5), and 7.98 (1H, s, 8-H).

Workup

  1. temperatureAfter cooling
  2. stirringthe solution was stirred for 30 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 (9:1)

Sources & evidence

ORD record
ord-4cd2b113550242c2b8d05cbb80c37189
Source dataset
uspto-grants-2003_06
Patent number
US06579981B1

Reaction notes

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