Sodium Carbonate → HCID 22508936, compound

HRID 2287352Notes

Reaction equation

HRID 2287352 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1B(O)O.[Cl:14][C:15]1[C:20]([N+:21]([O-:23])=[O:22])=[C:19](Cl)[N:18]=[C:17]([CH3:25])[N:16]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC=CC=1.[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>[Cl:14][C:15]1[C:20]([N+:21]([O-:23])=[O:22])=[C:19]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[C:2]([F:13])([F:12])[F:1])[N:18]=[C:17]([CH3:25])[N:16]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 831924,6-Dichloro-2-methyl-5-nitropyrimidineHCID 27343872-(Trifluoromethyl)benzeneboronic acid

Product 1

HCID 22508936HCID 22508936, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 241BenzeneSolvent

Procedure

Part A. A solution of 2-trifluoromethylphenylboronic acid (prepared according to the methods described in thee review by N. Miyaura and A. Suzuki, Chem. Rev. 1995, 95, p. 2457) (1.00 g, 5.27 mmol), 4,6-dichloro-2-methyl-5-nitropyrimidine (0.91 g, 4.39 mmol) and tetrakis(triphenyl-phosphine) palladium (147 mg) in benzene (15 mL) was treated with aq. sodium carbonate solution (6 mL, 1 M). This mixture was heated to reflux for 6 h, then cooled and partitioned between water and ethyl acetate (60 mL each). The organic layer was washed with brine, and the aqueous layers were back-extracted in sequence with more ethyl acetate. The organic extracts were combined, dried over sodium sulfate, filtered and evaporated. The residue was separated by column chromatography (silica gel, 15:85 ethyl acetate-hexane) to afford 4-chloro-2-methyl-5-nitro-6-(2-trifluoromethylphenyl)pyrimidine (0.64 g, 2.01 mmol, 38%) as a waxy solid. Spectral data: RF 0.40 (20:80 ethyl acetate-hexane). 1H NMR (300 MHz, CDCl3) 8 7.84-7.81 (1H, m), 7.69-7.53 (2H, m), 7.38-7.35 (1H, m), 2.84 (3H, s). MS (NH3 -CI) m/e 320 (24), 319 (26), 318 (100).

Workup

  1. temperatureThis mixture was heated
  2. temperatureto reflux for 6 h
  3. temperaturecooled
  4. custompartitioned between water and ethyl acetate (60 mL each)
  5. washThe organic layer was washed with brine
  6. extractionthe aqueous layers were back-extracted in sequence with more ethyl acetate
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue was separated by column chromatography (silica gel, 15:85 ethyl acetate-hexane)

Sources & evidence

ORD record
ord-2c08c63400ea4f0b91f14b1385b7cf86
Source dataset
uspto-grants-2000_07
Patent number
US06083948

Reaction notes

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