(2-Methoxy-4,6-dimethylphenyl)boronic acid → HCID 22490043, compound

HRID 2180005Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([O:8][CH3:9])[C:5]([OH:10])=[C:4]([CH3:11])[N:3]=1.[CH3:12][O:13][C:14]1[CH:19]=[C:18]([CH3:20])[CH:17]=[C:16]([CH3:21])[C:15]=1B(O)O>C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+].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>[CH3:9][O:8][C:6]1[C:5]([OH:10])=[C:4]([CH3:11])[N:3]=[C:2]([C:15]2[C:14]([O:13][CH3:12])=[CH:19][C:18]([CH3:20])=[CH:17][C:16]=2[CH3:21])[N:7]=1

Participants

Conditions

Temperature: 95 °C

Procedure

A mixture of 2-chloro-4-methoxy-6-methylpyrimidin-5-ol (348 mg, 2.0 mmol), 2-methoxy-4,6-dimethylphenylboronic acid (540 mg, 3.0 mmol), tetrakis(triphenylphosphine)palladium (0) (115 mg, 5 mol %) in toluene (12 mL) and sodium carbonate (1M in water, 4 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-methoxy-2-(6-methoxy-2,4-dimethylphenyl)-6-methylpyrimidin-5-ol as a white solid.

Workup

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

Sources & evidence

ORD record: ord-d8fc84db2620473d8f40827898f1aadb
Source dataset: uspto-grants-2005_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06887875B2

Reaction notes

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