ChemicalBook CAS DataBase List 3-(4-Phenoxy-phenyl)-1-piperidin-3-yl-1H-pyrazolo[3,4-d]pyriMidin-4-ylaMine

3-(4-Phenoxy-phenyl)-1-piperidin-3-yl-1H-pyrazolo[3,4-d]pyriMidin-4-ylaMine synthesis

6synthesis methods

Product Name:3-(4-Phenoxy-phenyl)-1-piperidin-3-yl-1H-pyrazolo[3,4-d]pyriMidin-4-ylaMine
CAS Number:1022150-12-4
Molecular formula:C22H22N6O
Molecular Weight:386.45

330786-24-8 Synthesis

3-(4-Phenoxyphenyl)-1h-pyrazolo[3,4-d]pyrimidin-4-amine

330786-24-8
445 suppliers
$55.00/100mg

143900-44-1 Synthesis

143900-44-1
551 suppliers
$5.00/1g

3-(4-Phenoxy-phenyl)-1-piperidin-3-yl-1H-pyrazolo[3,4-d]pyriMidin-4-ylaMine

1022150-12-4
271 suppliers
$180.00/1g

Yield:1022150-12-4 85%

Reaction Conditions:

with di-isopropyl azodicarboxylate;triphenylphosphine in tetrahydrofuran at 25;Inert atmosphere;Large scale;Mitsunobu Displacement;Temperature;

Steps:

10 Embodiment 10: intermediate -1: (R)-3 - (4 - phenoxy-phenyl) -1 - (piperidine -3 - yl) - 1H - pyrazolo [3,4-d]-4-
To 200L reaction kettle adding 124.60 kg tetrahydrofuran, are added under stirring 3 - (4 -)-1H-[34-D]-4-(SM1)(4.00kg1eq)(S)-1-Oxycarbonyl -3 - hydroxy piperidine (SM2) (7.96 kg, 3eq), triphenylphosphine (10.40 kg, 3eq). 25[...] (will be 8.00 kg, 3eq azo-phthalic acid diisopropyl ester soluble in 8.00 kg of in tetrahydrofuran),325(TLCMonitoring: ethyl acetate: methanol=10:1). Stirring under reduced pressure distillation. Temperature control 15 °C, dropwise 24.00kg325The reaction is complete (TLC monitoring: dichloromethane: ethyl acetate=5:3). Dichloromethane is used for extraction of the aqueous phase(60.00kg)45.00kgStirring 30 minutes later, the static layering, the minute eliminates upper organic phase. The remaining aqueous phase is added to the 200L anti-1535.00kg 20(9.60Kg sodium hydroxide into 38.40 kg of pure water), the use of pH test paper monitoring reaction solution, pH=5 - 6(2)100LAdding 19.20v ethanol, 0.10 kg of activated carbon, heated to 75 °C reflux stirring 2 hours. 1.60kg100LStop heating, water bath cooling, stirring crystallization, when the temperature is reduced to 25 °C, thermal crystallization 2 hours. 5.60kg6012Powder 3.75 kg, yield: 85%.

References:

Beijing Rui Chong Kang Tai Pharmaceutical Research Institute Limited;Gu, Huijuan;Chen, Yan;Zhang, Fan;Li, Wei;Liu, Xiangwei CN106146512, 2016, A Location in patent:Paragraph 0062; 0063

FullText