Pyrazolo[1,5-a]pyrimidine, 3-bromo-5,7-dichloro-

Base Information

• Chemical Name: Pyrazolo[1,5-a]pyrimidine, 3-bromo-5,7-dichloro-
• CAS No.: 114040-06-1
• Molecular Formula: C6H2BrCl2N3
• Molecular Weight: 266.91
• Hs Code.: 2933990090
• Mol file: 114040-06-1.mol

Synonyms:3-Bromo-5,7-dichloro-pyrazolo[1,5-a]pyrimidine; Pyrazolo[1,5-a]pyrimidine,3-bromo-5,7-dichloro;

Chemical Property of Pyrazolo[1,5-a]pyrimidine, 3-bromo-5,7-dichloro-

Chemical Property:

• Melting Point: 73-75 °C
• Refractive Index: 1.782
• PKA: -3.17±0.40(Predicted)
• PSA: 30.19000
• Density: 2.162 g/cm³
• LogP: 2.79860
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C

Purity/Quality:

99% ^*data from raw suppliers

3-Bromo-5,7-dichloro-pyrazolo[1,5-a]pyrimidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 3-Bromo-5,7-dichloro-pyrazolo[1,5-a]pyrimidine is an intermediate used in the synthesis of inhibitors of mitogen-activated protein kinase-activated protein kinase 2 as an antiinflammatory target.

Technology Process of Pyrazolo[1,5-a]pyrimidine, 3-bromo-5,7-dichloro-

There total 4 articles about Pyrazolo[1,5-a]pyrimidine, 3-bromo-5,7-dichloro- which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.0%

5,7-dichloropyrazolo[1,5-a]pyrimidine (57489-77-7) → 3-bromo-5,7-dichloropyrazolo[1,5-a]pyrimidine (114040-06-1)

Guidance literature:

With N-Bromosuccinimide; ammonium cerium(IV) nitrate; In acetonitrile; for 1h; Heating / reflux;

Reference yield:

pyrazolo[1,5-a]pyrimidine-5,7(4H,6H)-dione (672323-32-9) → 3-bromo-5,7-dichloropyrazolo[1,5-a]pyrimidine (114040-06-1)

Guidance literature:

Multi-step reaction with 2 steps

1: trichlorophosphate / N,N-dimethyl-aniline / 4 h / Reflux

2: N-Bromosuccinimide / acetonitrile / 2 h / 20 °C

With N-Bromosuccinimide; trichlorophosphate; In N,N-dimethyl-aniline; acetonitrile;

Reference yield:

5,7-dihydroxypyrazolo[1,5-a]pyrimidine (57489-70-0) → 3-bromo-5,7-dichloropyrazolo[1,5-a]pyrimidine (114040-06-1)

Guidance literature:

Multi-step reaction with 2 steps

1: trichlorophosphate; N,N-dimethyl-aniline / 18 h / Reflux

2: N-Bromosuccinimide / chloroform / 1 h / 20 °C

With N-Bromosuccinimide; N,N-dimethyl-aniline; trichlorophosphate; In chloroform;

DOI:10.1021/jm3013954

upstream raw materials:

5,7-dichloropyrazolo[1,5-a]pyrimidine

5,7-dihydroxypyrazolo[1,5-a]pyrimidine

pyrazolo[1,5-a]pyrimidine-5,7(4H,6H)-dione

Downstream raw materials:

tert-butyl (3-bromo-5-phenoxypyrazolo[1,5-a]pyrimidin-7-yl)((tetrahydro-2H-pyran-4-yl)methyl)carbamate

tert-butyl (3-(4-(cyclopropylcarbamoyl)-3-methylphenyl)-5-(phenylsulfonyl)pyrazolo[1,5-a]pyrimidin-7-yl)((tetrahydro-2H-pyran-4-yl)methyl)carbamate

tert-butyl (3-bromo-5-(phenylsulfonyl)pyrazolo[1,5-a]pyrimidin-7-yl)((tetrahydro-2H-pyran-4-yl)methyl)carbamate

C₂₉H₃₁N₅O₃

Refernces

• 1、 -. "PYRAZOLOPYRIMIDINE COMPOUNDS". Page/Page column 22; 23. . Retrieved 2015/06/03.
• 2、 Kosugi, Tomomi,Mitchell, Dale R.,Fujino, Aiko,Imai, Minoru,Kambe, Mika,Kobayashi, Shinji,Makino, Hiroaki,Matsueda, Yohei,Oue, Yasuhiro,Komatsu, Kanji,Imaizumi, Keiichiro,Sakai, Yuri,Sugiura, Satoshi,Takenouchi, Osami,Unoki, Gen,Yamakoshi, Yuko,Cunliffe, Vicky,Frearson, Julie,Gordon, Richard,John Harris,Kalloo-Hosein, Heidi,Le, Joelle,Patel, Gita,Simpson, Donald J.,Sherborne, Brad,Thomas, Peter S.,Suzuki, Naotaka,Takimoto-Kamimura, Midori,Kataoka, Ken-Ichiro. "Mitogen-activated protein kinase-activated protein kinase 2 (MAPKAP-K2) as an antiinflammatory target: Discovery and in vivo activity of selective pyrazolo[1,5- a ]pyrimidine inhibitors using a focused library and structure-based optimization approach". supporting information; scheme or table. p. 6700 - 6715. Retrieved 2012/09/25.