Potassium Carbonate → HCID 16220808, compound

HRID 403408Notes

Reaction equation

HRID 403408 reaction equation
[Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6](Cl)[N:5]=[CH:4][N:3]=1.[CH3:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1B(O)O.C(=O)([O-])[O-].[K+].[K+].C(=O)(O)[O-].[Na+]>O1CCOCC1>[Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[CH3:12])[N:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 203124,6-Dichloro-5-nitropyrimidineHCID 516892Sodium BicarbonateHCID 27332672-Methylphenyl boronic acid

Product 1

HCID 16220808HCID 16220808, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A stirring solution of 4,6-dichloro-5-nitropyrimidine (1.5 g, 7.73 mmol, CAS RN 4316-93-2), 2-methylphenyl boronic acid (1.16 g, 8.5 mmol), potassium carbonate (3.2 g, 23.2 mmol) and tetrakis-triphenylphosphine palladium(0) (447 mg, 0.30 mmol) in dioxane (50 mL) was heated under Argon atmosphere to 80° C. After 3 hours, the reaction mixture was cooled to room temperature and poured into saturated aqueous sodium bicarbonate solution and extracted three times with EtOAc. The combined organic layers were washed with brine and dried over MgSO4. Filtration followed by removal of volatiles gave a brown solid. Column chromatography on silica gel (50-75% ethyl acetate in n-hexane) provided the title compound gave 4-chloro-5-nitro-6-o-tolylpyrimidine (621 mg, 32%).

Workup

  1. extractionextracted three times with EtOAc
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationFiltration
  5. customfollowed by removal of volatiles
  6. customgave a brown solid

Sources & evidence

ORD record
ord-c7bc2b383f824138a1b3212ff95981a9
Source dataset
uspto-grants-2014_06
Patent number
US08748434B2

Reaction notes

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