تفاعل #1898897

معادلة التفاعل

2-(5-Benzyloxy-2-methylphenyl)-5,5-dimethyl[1,3,2]dioxaborinane

2-(5-benzyloxy-2-methylphenyl)-5,5-dimethyl-[1,3,2]dioxaborinane

2-amino-4,6-dichloropyrimidine

dimethoxyethane

sodium carbonate

→

4-(5-benzyloxy-2-methylphenyl)-6-chloropyrimidin-2-ylamine

المردود 40.0%

المذيبات

ethyl acetate

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةAfter cooling to room temperature
2. 2
   غسيلwashed with water (600 ml)
3. 3
   تجفيفThe ethyl acetate solution was dried over anhydrous magnesium sulfate
4. 4
   ترشيحAfter filtration
5. 5
   تركيزthe filtrate was concentrated under reduced pressure
6. 6
   أخرىThe resulting crude product was purified by silica gel column chromatography (developing solvent: n-hexane:ethyl acetate=6:1 to 3:1)

الإجراء التجريبي

2-(5-Benzyloxy-2-methylphenyl)-5,5-dimethyl[1,3,2]dioxaborinane (41.5 g) obtained in Step 2 above, 2-amino-4,6-dichloropyrimidine (13.8 g, 84.2 mmol), and dichloroditriphenylphosphine palladium (5.0 g, 7.12 mmol) were placed in a reaction vessel, and then dimethoxyethane (800 ml) and 2N aqueous sodium carbonate solution (63.1 ml, 126.2 mmol) were sequentially added thereto. The resulting mixture was stirred at 85° C. for 4 hours. After cooling to room temperature, the reaction solution was diluted with ethyl acetate (1000 ml), and washed with water (600 ml) and then with a saturated aqueous sodium chloride solution (60 ml). The ethyl acetate solution was dried over anhydrous magnesium sulfate. 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=6:1 to 3:1) to yield 4-(5-benzyloxy-2-methylphenyl)-6-chloropyrimidin-2-ylamine (10.84 g, 40%) as a pale yellow solid material.

المصدر