Sodium Carbonate → 5-(4-Methyl-3-nitrophenyl)-pyrimidine

HRID 1835454Notes

Reaction equation

HRID 1835454 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[N:6][CH:7]=1.[CH3:8][C:9]1[CH:14]=[CH:13][C:12](B(O)O)=[CH:11][C:10]=1[N+:18]([O-:20])=[O:19].C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.ClCCl.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:8][C:9]1[CH:14]=[CH:13][C:12]([C:2]2[CH:3]=[N:4][CH:5]=[N:6][CH:7]=2)=[CH:11][C:10]=1[N+:18]([O-:20])=[O:19]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 783445-BromopyrimidineHCID 27735154-Methyl-3-nitrobenzeneboronic acid

Product 1

HCID 235036635-(4-Methyl-3-nitrophenyl)-pyrimidineYield 84.2%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 6344DichloromethaneSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of 5-bromopyrimidine (1.59 g), 4-methyl-3-nitrophenylboronic acid (2.35 g) and tetrakis(triphenylphosphine)-palladium (578 mg) in 1,2-dimethoxyethane (20 ml) was added an aqueous solution of sodium carbonate (2M, 13 ml) followed by stirring at 80° C. for 24 hours. The mixture was diluted with dichloromethane and washed with water and brine. The organic layer was dried over magnesium sulfate and evaporated under reduced pressure. The residue was triturated with methanol. The resulting precipitated was collected by filtration, washed with methanol and diisopropyl ether and dried to give 5-(4-methyl-3-nitrophenyl)-pyrimidine (918 mg, 84.2%).

Workup

  1. washwashed with water and brine
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. customevaporated under reduced pressure
  4. customThe residue was triturated with methanol
  5. customThe resulting precipitated
  6. filtrationwas collected by filtration
  7. washwashed with methanol and diisopropyl ether
  8. customdried

Sources & evidence

ORD record
ord-0d28bd4737614e91b8fff875634505a8
Source dataset
uspto-grants-2004_08
Patent number
US06770667B1

Reaction notes

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