123148-78-7

Basic information

• Product Name: 4-Chloro-5-iodo-7H-pyrrol[2,3-d]pyrimidine
• Synonyms: 4-Chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine;4-CHLORO-5-IODO-7H-PYRROL[2,3]PYRIMIDINE;4-CHLORO-5-IODO-1H-PYRROLO [2,3-D] PYRIMIDINE;4-Chloro-5-iodo-7H-pyrrol[2,3-d]pyrimidine;6-Chloro-7-iodo-7-deazapurine;4-Chloro-5-iodo-1H-pyrrol...;7H-Pyrrolo[2,3-d]pyriMidine, 4-chloro-5-iodo-;6-Chloro-7-iodo-7-deazapurine,96%
• CAS NO: 123148-78-7
• Molecular Formula: C₆H₃ClIN₃
• Molecular Weight: 279.47
• EINECS: 2017-001-1
• Product Categories: Heterocycle-Pyrimidine series
• Mol File: 123148-78-7.mol
• Article Data: 75

Chemical Properties

• Melting Point: 179-183 °C
• Boiling Point: 241.0±50.0 °C(Predicted)
• Appearance: /
• Density: 2.284 g/cm³
• Refractive Index: 1.804
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 9.61±0.20(Predicted)
• Water Solubility: Insoluble in water.
• Sensitive: Light Sensitive
• CAS DataBase Reference: 4-Chloro-5-iodo-7H-pyrrol[2,3-d]pyrimidine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Chloro-5-iodo-7H-pyrrol[2,3-d]pyrimidine(123148-78-7)
• EPA Substance Registry System: 4-Chloro-5-iodo-7H-pyrrol[2,3-d]pyrimidine(123148-78-7)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38-R36/37/38-R22
• Safety Statements: 26-36/37-S36/37-S26-37
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 123148-78-7(Hazardous Substances Data)

Usage

Uses

6-Chloro-7-iodo-7-deazapurine is used as pharmaceutical intermediate.

InChI:InChI=1/C6H3ClIN3/c7-5-4-3(8)1-9-6(4)11-2-10-5/h1-2H,(H,9,10,11)

Upstream product

• 3680-69-1 4-chloro-1H-pyrrolo[2,3-d]pyrimidine 
• 516-12-1 N-iodo-succinimide 
• 3680-71-5 1H-pyrrolo[2,3-d]pyrimidin-4(7H)-one 
• 52133-67-2 ethyl 2-cyano-4,4-diethoxybutyrate 
• 7400-05-7 6-amino-5-(2,2-diethoxyethyl)-2-thioxo-2,3-dihydropyrimidin-4(1H)-one 
• 67831-84-9 2-thioxo-1,2,3,7-tetrahydro-4H-pyrrolo[2,3-d]pyrimidin-4-one 
• 1615680-91-5 6-chloro-5-((trimethylsilyl)ethynyl)pyrimidin-4-amine 
• 3680-71-5 7-deazahypoxanthine 
• 3680-71-5 Allopurinol 
• 162101-31-7 (2-fluoro-4-methoxyphenyl)boronic acid 
• 1207543-30-3 4‐chloro‐5‐iodo‐7‐((2‐(trimethylsilyl)ethoxy)methyl)‐7H‐pyrrolo[2,3‐d]pyrimidine 

Downstream Products

• 178420-94-5 (2R,3S,5R)-5-(4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2-(((4-methylbenzoyl)oxy)methyl)tetrahydrofuran-3-yl 4-methylbenzoate 
• 186301-25-7 4-N-phenylamino-5-iodo-7-(5-deoxy-2,3-O-isopropylidene-β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine 
• 186300-92-5 4-N-(4-fluorophenyl)amino-5-iodo-7-(5-deoxy-2,3-O-isopropylidene-β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine 
• 144928-17-6 GP683 
• 186394-14-9 (4-Fluoro-phenyl)-[5-phenyl-7-((3aR,4R,6R,6aR)-2,2,6-trimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-amine 
• 291759-34-7 4-N-phenylamino-5-phenyl-7-(5-deoxy-2,3-O-isopropylidene-β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine 
• 213744-81-1 4-chloro-5-iodo-7-isopropyl-7H-pyrrolo[2,3-d]pyrimidine 
• 911122-72-0 7-but-3-enyl-4-chloro-5-iodopyrrolo[2,3-d]pyrimidine 
• 699011-59-1 4-(1-methylhydrazino)-5-cyano-7-[(2,3,5-tri-O-benzoyl)-β-D-ribofuranosyl]-7H-pyrrolo[2,3-d]pyrimidine 
• 1379005-88-5 C₄₇H₅₁N₆O₆P 
• 258836-85-0 C₃₃H₂₈N₄O₅ 
• 258836-90-7 (2R,3S,5R)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(6H-2,3,5,6-tetraaza-aceanthrylen-2-yl)-tetrahydro-furan-3-ol 
• 258836-83-8 5',3'-di-O-p-toluoyl-6-chloro-7-N-(t-butoxycarbonyl)aniline-7-deazapurine-2'-deoxyriboside 
• 1392492-59-9 4-chloro-7-(5'-deoxy-α-D-xylofuranosyl)-5-iodo-pyrrolo[2,3-d]pyrimidine 

Relevant articles and documents

Study on the synthesis and PKA-I binding activities of 5-alkynyl tubercidin analogues

5-Alkynyl tubercidin analogues were synthesized and their biologica activities were evaluated. It was found that protein kinase A could be activated by 5-alkynyl tubercidin (9a) and cAMP- binding ability to PKA-I was selectively inhibited by it. Molecular

Synthesis of responsive fluorescent nucleobases 7-(benzofuran-2-yl)-7-deazahypoxanthine and 7-(benzofuran-2-yl)-7-deazaguanine using cross-coupling reaction

In order to develop fluorescent guanine analogs having substitutions at the 7-positions, 7-(benzofuran-2-yl)-7-deaza-hypoxanthine (1a) and 7-(benzofuran-2-yl)-7-deazaguanine (1b), were synthesized from 7-deaza-7-iodohypoxanthine and 7-deaza-7-iodo-2-N-pivaloylguanine via a Suzuki-Miyaura cross-coupling, respectively. Compound 1b showed strong fluorescence, with higher fluorescent quantum yields in less polar solvents; meanwhile, 1a showed higher activity in more polar solvents. It is expected that the guanine analogs can be incorporated into nucleosides to develop new fluorescent oligonucleotides.

Potent and selective EGFR inhibitors based on 5-aryl-7H-pyrrolopyrimidin-4-amines

The epidermal growth factor receptor represents an important target in cancer therapy, and low molecular weight inhibitors based on quinazolines have reached the marked. Herein we report on a new scaffold, 5-aryl-7H-pyrrolo[2,3-d]pyrimidin-4-amines, and show that when employing (S)-phenylglycinol as C-4 substituent, potent inhibitors can be made. The two most active inhibitors have suitable druglike properties, were equipotent with Erlotinib in Ba/F3 cell studies, and showed lower cross reactivity than Erlotinib in a panel of 50 kinases.

Synthesis and photophysical evaluation of new fluorescent 7-arylethynyl-7-deazaadenosine analogs

Three new fluorescent 7-deaza-2′-deoxyadenosine analogs were synthesized via the Sonogashira cross-coupling reaction of 7-iodo-7-deaza-2′-deoxyadenosine with 1-ethynylpyrene, 2-ethynyl-6-methoxynaphthalene, and 9-ethynylphenanthrene. The spectral properties of these analogs were evaluated in dioxane, EtOH, and H2O to determine their potential for use as environmentally sensitive fluorescent probes. All three analogs displayed large solvatofluorochromicity in H2O, relative to their emission wavelengths in dioxane or EtOH. Moreover, all three analogs exhibited microenvironmental sensitivity of their fluorescence emission intensity, being moderate to high quantum yields in dioxane and EtOH and significantly lower in H2O. Various attempts to perform domino cross-coupling and annuation reactions on 7-deaza-7-alkynyladenine derivatives to form a new fused tricyclic adenine analog were unsuccessful.

Selective C-H Iodination of (Hetero)arenes

Iodoarenes are versatile intermediates and common synthetic targets in organic synthesis. Here, we present a strategy for selective C-H iodination of (hetero)arenes with a broad functional group tolerance. We demonstrate the utility and differentiation to other iodination methods of supposed sulfonyl hypoiodites for a set of carboarenes and heteroarenes.

CYCLOALKYLIDENE CARBOXYLIC ACIDS AND DERIVATIVES AS BTK INHIBITORS

The present invention relates to novel cycloalkylidene carboxylic acids and derivatives thereof useful as Bruton tyrosine kinase (BTK) inhibitors. The present disclosure also relates to processes for their preparation, pharmaceutical compositions containing one or more such compounds, and to the use of such compounds and pharmaceutical compositions for the treatment of disorders involving mediation of BTK in humans (Formula I).