Synthesis of substituted 1h-pyrazolo[3,4-d]pyrimidines
A compound, unsubstituted technology, applied in the field of synthesis of substituted 1H-pyrazolo[3,4-d]pyrimidine compounds, can solve the problems of chiral piperidinylhydrazine derivatives such as expensive chiral chromatography steps
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Embodiment 1
[0127] Example 1: Synthesis of 4,6-dichloropyrimidine-5-formyl chloride
[0128]
[0129] In a three-necked round bottom flask with nitrogen inlet, 4,6-dichloropyrimidine-5-carboxylic acid (3.80 g, 1 eq.) was dissolved in diethyl ether (Et 2 (0) (60 mL), followed by the addition of dimethylformamide (DMF) (0.030 mL). After adding oxalyl chloride (2.03 mL, 1.2 eq.), the mixture was stirred at room temperature for 30 minutes. During this period, the escape of gas gradually ceased. The solvent was evaporated under reduced pressure to give the crude product, which was pure enough for the next step.
Embodiment 2
[0130] Embodiment 2: Synthesis of (4,6-dichloropyrimidin-5-yl) (4-phenoxyphenyl) ketone
[0131]
[0132] In a three-necked round bottom flask with nitrogen inlet, the acid chloride prepared in Example 1 was dissolved in CH 2 Cl 2 (220mL). Add AlCl 3 (7.25g, 2.5eq.) and diphenyl ether (8.97mL, 2.6eq.), a pale yellow suspension was obtained. The reaction mixture was stirred overnight at 50 °C, then poured into 400 mL of ice water. The phases were separated and the aqueous layer was washed with CH 2 Cl 2 (1x) extraction. The combined organic layers were washed with H 2 Washed with O (2x), saturated NaCl solution (2x), dried over anhydrous sodium sulfate, filtered and evaporated. The crude product was purified by column chromatography (cyclohexane / ethyl acetate 25:1) to give the product as a colorless crystalline solid. pass 1 The product was identified by H NMR and the following peaks were obtained:
[0133] 1 H NMR (500MHz, d 6 -DMSO)=9.14(s,1H),8.01(d,J=8.85Hz,...
Embodiment 3
[0134] Example 3: Synthesis of (4-amino-6-chloropyrimidin-5-yl) (4-phenoxyphenyl)-methanone
[0135]
[0136] In a Schlenk type flask, the ketone prepared in Example 2 (1.0 g, 1 eq.) was dissolved in toluene (70 mL). The reaction vessel was evacuated, backfilled three times with nitrogen, then finally evacuated and filled with NH 3 (airbag) refill. The reaction mixture was vigorously stirred overnight at 60 °C. Then, the solvent was evaporated under reduced pressure to give the product as an almost colorless crystalline solid. pass 1 The product was identified by H NMR and the following peaks were obtained:
[0137] 1 H NMR (500MHz, C 6 D. 6 )=8.10(s,1H),7.37(d,J=8.85Hz,2H),6.82(t,J=7.93Hz,2H),6.68(t,J=7.43Hz,1H),6.64–6.61(m , 2H), 6.50 (d, J=8.85Hz, 2H), 4.65 (br s, 2H).
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