Sodium Carbonate → HCID 10271246, compound

HRID 2180006Notes

Reaction equation

HRID 2180006 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH2:9]S([O-])(=O)=O)=[C:7]([CH3:14])[N:6]=[C:5]([C:15]2[C:20]([O:21][CH3:22])=[CH:19][C:18]([CH3:23])=[CH:17][C:16]=2[CH3:24])[N:4]=1.COC1[CH:32]=[C:31]([F:33])[CH:30]=[CH:29][C:28]=1B(O)O.[C:37](=[O:40])([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:33][C:31]1[CH:30]=[CH:29][C:28]([O:40][CH3:37])=[C:9]([C:8]2[C:3]([O:2][CH3:1])=[N:4][C:5]([C:15]3[C:20]([O:21][CH3:22])=[CH:19][C:18]([CH3:23])=[CH:17][C:16]=3[CH3:24])=[N:6][C:7]=2[CH3:14])[CH:32]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 2782672(4-Fluoro-2-methoxyphenyl)boronic acidHCID 86588569HCID 86588569, compound

Product 1

HCID 10271246HCID 10271246, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of 4-methoxy-2-(6-methoxy-2,4-dimethylphenyl)-6-methylpyrimidin-5-ylmethylsulfonate (203 mg, 0.5 mmol), 2-methoxy-4-fluorophenylboronic acid (169 mg, 1.0 mmol), tetrakis(triphenylphosphine)palladium(0) (29 mg, 5 mol %) in toluene (5 mL) and sodium carbonate (1M in water, 2 mL) is heated at 95° C. (oil bath temperature) in a pressure tube for 14 hours. The reaction is cooled to room temperature, diluted with ethyl acetate, washed with NaOH (2M) and then brine (2×50 mL). The solvents are dried (sodium sulfate) and removed under reduced pressure. Flash chromatography of the crude product (50% ethyl acetate in hexanes) yields 4-fluoro-1-methoxy-2-[4-methoxy-2-(6-methoxy-2,4-dimethylphenyl)-6-methylpyrimidin-5-yl]benzene (Compound 7) as an oil. MS: 383. NMR (400 MHz, CDCl3): 2.14 (s, 3H), 2.28 (s, 3H), 2.35 (s, 3H), 3.76 (s, 3H), 3.77 (s, 3H), 3.88 (s, 3H), 6.66 (s, 1H), 6.70 (s, 1H), 6.91-6.98 (m, 2H), 7.04-7.09 (m, 1H).

Workup

  1. temperatureThe reaction is cooled to room temperature
  2. washwashed with NaOH (2M)
  3. dry with materialThe solvents are dried (sodium sulfate)
  4. customremoved under reduced pressure

Sources & evidence

ORD record
ord-0256d9f84a514caa804195984ed0d23e
Source dataset
uspto-grants-2005_05
Patent number
US06887875B2

Reaction notes

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