Potassium Carbonate → HCID 59351773, compound

HRID 1889420Notes

Reaction equation

HRID 1889420 reaction equation
[Cl:1][C:2]1[NH:7][C:6](=[O:8])[NH:5][C:4](=[O:9])[CH:3]=1.Br[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[C:19]([C:24]#[N:25])=[CH:20][CH:21]=[CH:22][CH:23]=2)=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+].[OH-].[Na+]>C1(C)C=CC=CC=1.CS(C)=O>[Cl:1][C:2]1[N:7]([CH2:11][C:12]2[CH:13]=[CH:14][C:15]([C:18]3[C:19]([C:24]#[N:25])=[CH:20][CH:21]=[CH:22][CH:23]=3)=[CH:16][CH:17]=2)[C:6](=[O:8])[NH:5][C:4](=[O:9])[CH:3]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 732726-ChlorouracilHCID 15019124'-(Bromomethyl)-2-cyanobiphenyl

Product 1

HCID 59351773HCID 59351773, compoundYield 56.5%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 1140TolueneSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 6-chloropyrimidine-2,4(1H,3H)-dione (10 g), 4′-(bromomethyl)biphenyl-2-carbonitrile (4.71 g), potassium carbonate (27.8 g) and dimethyl sulfoxide (100 mL) was stirred at 65° C. for 2 hr. To the reaction mixture were added 1N aqueous sodium hydroxide solution (70 mL) and toluene (50 mL), and the mixture was cooled to 0° C. The precipitated solid was recrystallized from methanol to give the title compound as colorless crystals (3.3 g, 14%).

Workup

  1. temperaturethe mixture was cooled to 0° C
  2. customThe precipitated solid was recrystallized from methanol

Sources & evidence

ORD record
ord-a1bafbec63804fd883f212f9836397a2
Source dataset
uspto-grants-2013_08
Patent number
US08501750B2

Reaction notes

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