Sodium Carbonate → HCID 86728325, compound

HRID 2171346Notes

Reaction equation

HRID 2171346 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[NH:11][CH2:10][CH2:9][N:5]2[C:6](=[O:8])[N:7]=1.[CH:12]1(B(O)O)[CH2:14][CH2:13]1.N1C=CC(C2C=CN=CC=2)=CC=1.C([O-])([O-])=O.[Na+].[Na+]>ClCCCl.C([O-])(=O)C.[Cu+]>[Cl:1][C:2]1[CH:3]=[C:4]2[N:11]([CH:12]3[CH2:14][CH2:13]3)[CH2:10][CH2:9][N:5]2[C:6](=[O:8])[N:7]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 111074,4'-BipyridineHCID 2760897Cyclopropylboronic acidHCID 135743575HCID 135743575, compound

Product 1

HCID 86728325HCID 86728325, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 69023Cuprous acetateCatalystHCID 111,2-DichloroethaneSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 7-chloro-2,3-dihydroimidazo[1,2-c]pyrimidin-5(1H)-one (300 mg, 1.75 mmol), cyclopropylboronic acid (300 mg, 3.50 mmol), 4,4′-bipyridine (273 mg, 1.75 mmol), copper (I) acetate (214 mg, 1.75 mmol) and Na2CO3 (371 mg, 3.50 mmol) in 1,2-dichloroethane (DCE) (20 mL) was stirred at 70° C. for 3 h and concentrated to remove solvent under vacuo. Purification via Biotage system with inverse phase column (water and acetonitrile as eluent) afforded the title product (200 mg).

Workup

  1. concentrationconcentrated
  2. customto remove solvent under vacuo
  3. customPurification via Biotage system with inverse phase column (water and acetonitrile as eluent)

Sources & evidence

ORD record
ord-e83dd41931ce4ff0a4f625fa64a1e067
Source dataset
uspto-grants-2015_06
Patent number
US09051325B2

Reaction notes

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