Sodium Bicarbonate → HCID 178509046, compound

HRID 2269043Notes

Reaction equation

HRID 2269043 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]([S:11][CH2:12][CH2:13][CH:14]2OCC[O:15]2)[N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([OH:26])[N:6]2[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(=O)([O-])O.[Na+]>Cl.O1CCCC1>[NH2:1][C:2]1[N:10]=[C:9]([S:11][CH2:12][CH2:13][CH:14]=[O:15])[N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([OH:26])[N:6]2[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 178509042HCID 178509042, compound

Product 1

HCID 178509046HCID 178509046, compoundYield 44%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

6-Amino-9-benzyl-2-[2-(1,3-dioxolan-2-yl)ethyl)thio-8-hydroxypurine (74 mg, 0.20 mmol) was dissolved in a mixture of 3.3N hydrochloric acid (1 ml) and tetrahydrofuran (4 ml). The solution was stirred at 70° C. for 7 hours and then neutralized with aqueous sodium hydrogen carbonate. After removal of tetrahydrofuran in vacuo, the resulting crystals were filtered, purified by silica gel chromatography (5% methanol/chloroform) to give the subject compound (17 mg, yield 44%).

Workup

  1. customAfter removal of tetrahydrofuran in vacuo
  2. filtrationthe resulting crystals were filtered
  3. custompurified by silica gel chromatography (5% methanol/chloroform)

Sources & evidence

ORD record
ord-32fb8013b27a4f0693988296163adef5
Source dataset
uspto-grants-2001_12
Patent number
US06329381B1

Reaction notes

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