Hydrochloric Acid → HCID 68007553, compound

HRID 1027785Notes

Reaction equation

HRID 1027785 reaction equation
Cl[C:2]1[N:10]=[C:9]2[C:5]([NH:6][C:7](=[O:12])[N:8]2[CH3:11])=[CH:4][N:3]=1.[C:13]1(/[CH:19]=[CH:20]/B(O)O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+].Cl>CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C.CN1CCCC1=O>[CH3:11][N:8]1[C:7](=[O:12])[NH:6][C:5]2[C:9]1=[N:10][C:2](/[CH:20]=[CH:19]/[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[N:3][CH:4]=2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 5702628Styrylboronic acidHCID 82406358HCID 82406358, compound

Product 1

HCID 68007553HCID 68007553, compound

Reagents, catalysts & solvents 2

HCID 178418851HCID 178418851, compoundCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
150 °C

Procedure

To a mixture of 2-chloro-9-methyl-7,9-dihydro-8H-purine-8-one <the compound of Reference Example 1> (200 mg), trans-2-phenylvinylboronic acid (192 mg), potassium carbonate (448 mg) and 1-methylpyrrolidin-2-one (3 ml) was added bis(tri-tert-butylphosphine)palladium (28 mg) under nitrogen atmosphere and the mixture was stirred at 150° C. under microwave irradiation for 1 hour. To the reaction mixture was added 1 mol/L hydrochloric acid (50 ml) and the crude solids precipitated were collected by filtration. The obtained crude solids were purified by silica gel column chromatography (eluent: chloroform/methanol=100/0˜90/10) to give the title compound 179 mg.

Workup

  1. customthe crude solids precipitated
  2. filtrationwere collected by filtration
  3. customThe obtained crude solids
  4. customwere purified by silica gel column chromatography (eluent: chloroform/methanol=100/0˜90/10)

Sources & evidence

ORD record
ord-f8fd9a3d9179448aa2b30077608bf16b
Source dataset
uspto-grants-2014_05
Patent number
US08735406B2

Reaction notes

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