Triphenylphosphine → HCID 59224675, compound

Temperature

80 °C

2-Amino-4,6-dichloropyrimidine (246 mg, 1.5 mmol), palladium acetate (17 mg, 0.07 mmol), triphenylphosphine (59 mg, 0.22 mmol), sodium bicarbonate (168 mg, 2.0 mmol), 1,2-dimethoxyethane (2.5 ml), and water (1.0 ml) were placed in a reaction vessel. The resulting mixture was stirred at 80° C. for 10 minutes. A 1,2-dimethoxyethane (2.5 ml) solution of 2-methoxy-4-methyl-5-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)benzoic acid methyl ester (294 mg, 1.0 mmol) obtained in Step 3 above was added dropwise to the mixture. The resulting mixture was stirred at 80° C. for 14 hours. The reaction solution was diluted with ethyl acetate (100 ml), and washed three times with water (40 ml), and then with a saturated aqueous sodium chloride solution (40 ml). The washed ethyl acetate solution was dried over anhydrous sodium sulfate (10 g). After filtration, the filtrate was concentrated under reduced pressure. The resulting crude product was purified by silica gel column chromatography (developing solvent: n-hexane:ethyl acetate=2:1) to yield 5-(2-amino-6-chloropyrimidin-4-yl)-2-methoxy-4-methylbenzoic acid methyl ester (Compound 1-2) (164 mg) as a yellow solid material.

1. stirringThe resulting mixture was stirred at 80° C. for 14 hours
2. washwashed three times with water (40 ml)
3. dry with materialThe washed ethyl acetate solution was dried over anhydrous sodium sulfate (10 g)
4. filtrationAfter filtration
5. concentrationthe filtrate was concentrated under reduced pressure
6. customThe resulting crude product was purified by silica gel column chromatography (developing solvent: n-hexane:ethyl acetate=2:1)

ORD record

ord-8cd02d85dc874fe6af22bc722f87e0c6

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08362236B2