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151266-23-8

151266-23-8 Structure

151266-23-8 Structure
IdentificationBack 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 PropertiesBack 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
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H335-H315-H319
[Precautionary statements ]

P261-P280a-P304+P340-P305+P351+P338-P405-P501a-P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313
[Hazard Codes ]

Xn
[Risk Statements ]

36/37/38-22
[Safety Statements ]

26-36/37/39-37
[TSCA ]

N
[REACH Registrations]

Active
[HS Code ]

29335990
[Storage Class]

11 - Combustible Solids
[Hazard Classifications]

Acute Tox. 4 Oral
Hazard InformationBack 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
Spectrum DetailBack Directory
[Spectrum Detail]

4-AMINO-3-IODO-1H-PYRAZOLO[3,4-D]PYRIMIDINE(151266-23-8)1HNMR
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