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

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

카스 번호330786-24-8

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

CBNumberCB72648137

분자식C17H13N5O

포뮬러 무게303.32

MOL 파일330786-24-8.mol

화학적 성질

녹는점	>262oC (dec.)
끓는 점	577.4±50.0 °C(Predicted)
밀도	1.380±0.06 g/cm3(Predicted)
저장 조건	Keep in dark place,Inert atmosphere,Room temperature
용해도	DMSO(약간 용해됨), 에탄올(약간 용해됨)
산도 계수 (pKa)	10.40±0.30(Predicted)
물리적 상태	고체
물리적 상태	단단한 모양
색상	옅은 갈색에서 갈색까지
InChI	InChI=1S/C17H13N5O/c18-16-14-15(21-22-17(14)20-10-19-16)11-6-8-13(9-7-11)23-12-4-2-1-3-5-12/h1-10H,(H3,18,19,20,21,22)
InChIKey	YYVUOZULIDAKRN-UHFFFAOYSA-N
SMILES	C1=NC(N)=C2C(C3=CC=C(OC4=CC=CC=C4)C=C3)=NNC2=N1

그림문자(GHS)

3-(4-Phenoxyphenyl)-1h-pyrazolo[3,4-d]pyrimidin-4-amine 화학적 특성, 용도, 생산

개요
5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyriMidin-4-ylaMine, also known as ibrutinib N-2, is a light brown solid. It can be prepared from 3-Iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine and 4-phenoxybenzeneboronicacid by Suzuki coupling reaction[1]. Ibrutinib N-2 is often used in the preparation of the marketed drug PCI-32765 (IMBRUVICAVR)[2]. PCI-32765 is aIbrutinib -BTK inhibitor and can be used as an anticancer drug to treat B cell cancers like mantle cell lymphoma and chronic lymphocytic leukemia.
용도
As Ibrutinib intermediates, 5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyriMidin-4-ylaMine can be used as organic synthesis intermediates and pharmaceutical intermediates, mainly used in laboratory research and development and chemical production processes.
주요 응용
3-(4-Phenoxyphenyl)-1h-pyrazolo[3,4-d]pyrimidin-4-amine is an intermediate for the synthesis of ibrutinib, which is mainly used in drug synthesis and related experimental studies.
Synthesis

2 g of 3-iodo-4-aminopyrazolo[3,4-d]pyrimidine (7.7 mmol),3.28 g p-phenoxybenzeneboronic acid (15.4 mmol)And 5.28 g of K3PO4 (23.0 mmol) were dissolved in 25 mL of dioxane and 10 mL of water.After stirring for 5-8 minutes, argon gas was passed for 20 minutes.An additional 1.4 g of tetrakis(triphenylphosphine)palladium (1.2 mmol) was added.After heating again for 10 minutes, the heating was started, and the reaction was carried out at 120 ?? C for 24 hours.After the reaction was completed, it was cooled to room temperature, stirred for 24 hours to wait for product to precipitate, and the reaction mixture was washed with 25 mL of water and filtered.The filtered solid was again washed with 75 ml of methanol, washed with 50 mL of ethanol, and dried in a dry box.There was obtained 1.75 g of 3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidine-4-amine in a yield of 75%.
참고 문헌
[1] Rampalli, S, et al. Process for the Preparation of Ibrutinib. PCT Int. Appl. 2017; 134588.
[2] Dasar G, et al. One-step synthesis of magnetically recyclable palladium loaded magnesium ferrite nanoparticles: application in synthesis of anticancer drug PCI-32765. Inorganic and Nano-Metal Chemistry, 2020; 50.

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