Hydrochloric Acid → HCID 57642844, compound

HRID 2112882Notes

Reaction equation

HRID 2112882 reaction equation
[CH2:1]([N:5]1[C:13]2[C:8](=[N:9][C:10]([Cl:15])=[N:11][C:12]=2Cl)[N:7]([CH3:16])[C:6]1=[O:17])[C:2]#[C:3][CH3:4].[C:18]([O:22][C:23]([N:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1)=[O:24])([CH3:21])([CH3:20])[CH3:19].C(N(CC)CC)C.Cl>C(#N)C.O>[C:18]([O:22][C:23]([N:25]1[CH2:30][CH2:29][N:28]([C:12]2[N:11]=[C:10]([Cl:15])[N:9]=[C:8]3[C:13]=2[N:5]([CH2:1][C:2]#[C:3][CH3:4])[C:6](=[O:17])[N:7]3[CH3:16])[CH2:27][CH2:26]1)=[O:24])([CH3:21])([CH3:19])[CH3:20]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 23085375HCID 23085375, compound

Product 1

HCID 57642844HCID 57642844, compoundYield 60.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

7-(2-Butynyl)-2,6-dichloro-9-methyl-7,9-dihydropurin-8-one (334 mg) was dissolved in acetonitrile (5 mL), piperazin-1-carboxylic acid t-butyl ester (300 mg) and triethylamine (190 μL) were added, and this reaction solution was stirred at room temperature for 96 hours. After completion of the reaction, 1 N hydrochloric acid (3 mL) and water (10 mL) were added to the reaction solution, and this was extracted with ethyl acetate. The obtained organic layer was washed sequentially with water and saturated brine, and dried over anhydrous magnesium sulfate. The resulting 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 (312 mg).

Workup

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

Sources & evidence

ORD record
ord-cb70859f25b94a839d3792a6b9d2d8c7
Source dataset
uspto-grants-2009_04
Patent number
US07524847B2

Reaction notes

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