Water → 3-(2-Chloropyrimidin-4-yl)-6-methoxy-2-methylbenzaldehyde

HRID 873545Notes

Reaction equation

C(=O)([O-])[O-].[Na+].[Na+].[CH3:7][O:8][C:9]1[C:14]([CH:15]=[O:16])=[C:13]([CH3:17])[C:12](B2OC(C)(C)C(C)(C)O2)=[CH:11][CH:10]=1.[Cl:27][C:28]1[N:33]=[C:32](Cl)[CH:31]=[CH:30][N:29]=1.O>C(COC)OC>[Cl:27][C:28]1[N:33]=[C:32]([C:12]2[C:13]([CH3:17])=[C:14]([C:9]([O:8][CH3:7])=[CH:10][CH:11]=2)[CH:15]=[O:16])[CH:31]=[CH:30][N:29]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A 2 M aqueous solution of sodium carbonate (2.72 mL, 5.43 mol) and tetrakistriphenylphosphine palladium(0) (209 mg, 0.181 mmol) were added to a suspension of the 6-methoxy-2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde obtained in Example 4-1 (500 mg, 1.81 mmol) and 2,4-dichloropyrimidine (405 mg, 2.72 mmol) in dimethoxyethane (5.4 mL) at room temperature. The mixture thus obtained was stirred at 80° C. for 10 hours. Thereafter, the resulting solution was cooled to room temperature. Water was added to the reaction solution, and the precipitated crude product was collected by filtration and was then washed with water and diisopropyl ether to obtain the title compound (418 mg, yield: 88%).

Workup

customThe mixture thus obtained
temperatureThereafter, the resulting solution was cooled to room temperature
customthe precipitated crude product
filtrationwas collected by filtration
washwas then washed with water and diisopropyl ether

Sources & evidence

ORD record: ord-10d6b4bbc5034e4f8f60272012c2420a
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08975263B2

Reaction notes

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