Hydrochloric Acid → HCID 57642863, compound

HRID 2112894Notes

Reaction equation

HRID 2112894 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[N:22]=[C:21]([Cl:23])[N:20]=[C:19]3[C:15]=2[N:16]([CH2:33][C:34]#[C:35][CH3:36])[C:17](=[O:32])[N:18]3COC(=O)C(C)(C)C)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Cl>CO.O1CCCC1>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([C:14]2[N:22]=[C:21]([Cl:23])[N:20]=[C:19]3[C:15]=2[N:16]([CH2:33][C:34]#[C:35][CH3:36])[C:17](=[O:32])[NH:18]3)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 57642852HCID 57642852, compound

Product 1

HCID 57642863HCID 57642863, compoundYield 56.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-[7-(2-Butynyl)-2-chloro-9-(2,2-dimethylpropionyloxymethyl)-8-oxo-8,9-dihydro-7H-purin-6-yl]piperazine-1-carboxylic acid t-butyl ester (665 mg) was dissolved in a mixed solvent of methanol (5 mL) and tetrahydrofuran (3 mL), and then sodium hydride (60-72% in oil) (61 mg) was added to this solution. The reaction solution was stirred at room temperature for three hours. 1 N aqueous hydrochloric acid (3 mL) was then added to the reaction solution, which was extracted using ethyl acetate. The obtained organic layer was washed sequentially with water and saturated brine, and then dried over anhydrous magnesium sulfate. The organic layer was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:3) to give the title compound (294 mg).

Workup

  1. extractionwas extracted
  2. washThe obtained organic layer was washed sequentially with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationThe organic layer was concentrated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:3)

Sources & evidence

ORD record
ord-5025f59447fc4a8da8b145bda6b732b4
Source dataset
uspto-grants-2009_04
Patent number
US07524847B2

Reaction notes

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