| Identification | Back Directory | [Name]
4-AMINO-3-IODO-1H-PYRAZOLO[3,4-D]PYRIMIDINE | [CAS]
151266-23-8 | [Synonyms]
7-Iodo-7-deaza-8-aza-adenine
4-AMINO-3-IODO-1H-PYRAZOLO[3
4-AMino-3-iodopyrazolo[3,4-d]pyridine
3-iodo-4-Aminopyrazolo[3,4-d]pyridine
3-iodopyrazolo[3,4-d]pyriMidin-4-aMine
4-Amino-3-iodopyrazolo[3,4-d]pyrimidine
4-Amino-3-iodo-1H-pyrazolo[3,4-D]pyridine
3-iodo-4-AMino-1H-pyrazolo[3,4-d]pyridine
3-iodo-2H-pyrazolo[3,4-d]pyrimidin-4-amine
3-iodo-4-aMino-1H-pyrazolo[3,4-d]pyriMidine
4-AMINO-3-IODO-1H-PYRAZOLO[3,4-D]PYRIMIDINE
3-IODO-1H-PYRAZOLO[3,4-D]PYRIMIDIN-4-YLAMINE
1H-Pyrazolo[3,4-d]pyrimidin-4-amine, 3-iodo-
3-Iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine >
4-AMINO-3-IODO-1H-PYRAZOLO[3,4-D]PYRIMIDINE ISO 9001：2015 REACH | [Molecular Formula]
C5H4IN5 | [MDL Number]
MFCD03787931 | [MOL File]
151266-23-8.mol | [Molecular Weight]
261.02 |
| Chemical Properties | Back Directory | [Boiling point ]
312.3±52.0 °C(Predicted) | [density ]
2.92±0.1 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [form ]
powder to crystal | [pka]
10.50±0.20(Predicted) | [color ]
White to Light yellow to Light orange | [Sensitive ]
Light Sensitive | [λmax]
282nm(lit.) | [InChI]
InChI=1S/C5H4IN5/c6-3-2-4(7)8-1-9-5(2)11-10-3/h1H,(H3,7,8,9,10,11) | [InChIKey]
HQAIUXZORKJOJY-UHFFFAOYSA-N | [SMILES]
C1=NC(N)=C2C(I)=NNC2=N1 |
| Hazard Information | Back Directory | [Description]
3-Iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine is a key intermediate in the synthesis of ibrutinib.
| [Uses]
3-Iodo-3H-pyrazolo[3,4-d]pyrimidin-4-amine acts as a reagent in the discovery and preparation of CHMFL-FLT3-122 as potent and orally available FLT3 kinase inhibitor for FLT3-ITD positive acute myeloid leukemia. Development and preparation of potent and selective Plasmodium falciparum calcium-dependent protein kinase 4 (PfCDPK4) inhibitors that block the transmission of malaria to mosquitoes. | [Synthesis]
A solution of 3H-pyrazolo[3,4-d]pyrimidin-4-amine (10 g, 0.074 mol) and n-iodo-succinamide (25 g, 0.111 mol) in DMF (80 mL) was heated to 80° C. overnight under an argon atmosphere. The resulting solid was filtered and rinsed with cold EtOH. The product was dried in vacuo overnight to yield 3-Iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine (24 g, 100 per cent yield). | [References]
[1] Patent: US2007/293516, 2007, A1. Location in patent: Page/Page column 12; 16
[2] Angewandte Chemie - International Edition, 2016, vol. 55, # 36, p. 10909 - 10912
[3] Angew. Chem., 2016, vol. 128, p. 11069 - 11073,5
[4] Journal of Medicinal Chemistry, 2017, vol. 60, # 18, p. 7725 - 7744
[5] Patent: US2012/202785, 2012, A1. Location in patent: Page/Page column 258 |
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