Hydrochloric Acid → HCID 9836155, compound

HRID 271272Notes

Reaction equation

HRID 271272 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:14]=[C:13]([NH2:15])[N:12]=[C:11]2[C:7]=1[N:8]=[CH:9][N:10]2[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-])=O)[CH:18]=1.O.O.Cl[Sn]Cl.Cl.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[OH-].[Na+]>CCO>[NH2:23][C:19]1[CH:18]=[C:17]([CH:22]=[CH:21][CH:20]=1)[CH2:16][N:10]1[CH:9]=[N:8][C:7]2[C:11]1=[N:12][C:13]([NH2:15])=[N:14][C:6]=2[C:2]1[O:1][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 61436Stannous chloride dihydrateHCID 2724141Tetrabutylammonium FluorideHCID 44449695HCID 44449695, compound

Product 1

HCID 9836155HCID 9836155, compoundYield 26.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 6-(2-furyl)-9-(3-nitrobenzyl)-9H-purine-2-amine (400 mg, 1.12 mmol) in EtOH (10 mL) at 50° C. was treated with a solution of SnCl2.2H2O (808 mg, 3.58 mmol) in conc.HCl (1.8 mL, 21.42 mmol), stirred for 1.5 h, cooled, basified to pH 10 (1-M NaOH) and the resulting solid was filtered, suspended in methanol, treated with HCl in dioxane (4-M, 2 mL), diluted with diethyl ether and filtered to give the title compound (90 mg, 22%) as a yellow solid.

Workup

  1. temperaturecooled
  2. filtrationthe resulting solid was filtered
  3. additiontreated with HCl in dioxane (4-M, 2 mL)
  4. additiondiluted with diethyl ether
  5. filtrationfiltered

Sources & evidence

ORD record
ord-c48b1b18a1414417988d695eb962bee1
Source dataset
uspto-grants-2008_11
Patent number
US07452894B2

Reaction notes

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