Potassium Carbonate → HCID 18756242, compound

HRID 433923Notes

Reaction equation

HRID 433923 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[OH:9].C(=O)([O-])[O-].[K+].[K+].[Cl:16][C:17]1[CH:22]=[C:21](Cl)[N:20]=[CH:19][N:18]=1>CS(C)=O>[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[O:9][C:21]1[CH:22]=[C:17]([Cl:16])[N:18]=[CH:19][N:20]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 231092-Bromo-4-methylphenolHCID 709434,6-Dichloropyrimidine

Product 1

HCID 18756242HCID 18756242, compoundYield 71.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 2-bromo-4-methylphenol (500 mg), in dimethyl sulphoxide (2 ml), was added freshly ground potassium carbonate (407 mg). The mixture was stirred for 20 minutes, and 4,6-dichloropyrimidine (432 mg) was added. The mixture was stirred at ambient temperature for 2 hours, and the reaction mixture preadsorbed onto silica gel (1 g) and purified by column chromatography (eluting with 10% ethyl acetate/dichloromethane) to yield a gum (571 mg, 71%). NMR: 2.35 (3H, s), 7.25 (2H, s), 7.5 (1H, s), 7.55 (1H, s), 8.7 (1H, s); MS; (electrospray) 451 (MH)+.

Workup

  1. stirringThe mixture was stirred at ambient temperature for 2 hours
  2. custompurified by column chromatography (eluting with 10% ethyl acetate/dichloromethane)

Sources & evidence

ORD record
ord-ee6a46ab75cb460f8bb9792e2414140a
Source dataset
uspto-grants-2003_12
Patent number
US06670368B1

Reaction notes

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