271-70-5

Usage

Uses

Used in Pharmaceutical Industry:
DEAZAPURINE is used as an active pharmaceutical ingredient for the development of antibiotics such as tubercidin and toyocamycin. These antibiotics are effective against certain bacterial infections, providing an essential tool in the treatment of diseases.
Used in Biochemistry Research:
DEAZAPURINE is used as a research tool for studying the structure and function of nucleic acids, coenzymes, and high-energy compounds. Its unique structure allows scientists to investigate the role of nitrogen atoms in these molecules and their impact on cellular metabolism.
Used in Coenzyme Production:
DEAZAPURINE is used as a precursor in the synthesis of coenzymes like coenzyme F420. These coenzymes play a crucial role in various metabolic pathways, including those involved in energy production and electron transfer.
Used in TRNA Synthesis:
DEAZAPURINE is used as a component in the assembly of transfer RNAs (tRNAs). tRNAs are essential for protein synthesis, as they carry specific amino acids to the ribosome during translation, ensuring the correct sequence of amino acids in the resulting protein.

InChI:InChI=1/C6H5N3/c1-2-8-6-5(1)3-7-4-9-6/h1-4H,(H,7,8,9)

Synthetic route

4-chloro-1H-pyrrolo[2,3-d]pyrimidine (3680-69-1) → 7H-pyrrolo[2,3-d]pyrimidine (271-70-5)

Conditions	Yield
With hydrogen; palladium 10% on activated carbon In methanol under 760.051 Torr; for 16h;	98%
With ammonium formate; 20% Pd(OH)2 on carbon In methanol for 2h; Heating / reflux;	97%
With hydrogen; palladium on activated charcoal	84%
With ammonium hydroxide; hydrogen; palladium on activated charcoal In ethanol at 20℃; for 6h;	83.7%
With hydrogen; palladium 10% on activated carbon In methanol at 20℃;

(Z)-4-acetylamino-5-(2-ethoxyethenyl)pyrimidine → 7H-pyrrolo[2,3-d]pyrimidine (271-70-5)

Conditions	Yield
With hydrogenchloride In methanol for 0.5h; Heating;	71%

3,7-Dihydro-4H-pyrrolo<2,3-d>pyrimidin-4-thion (1421-27-8) → 7H-pyrrolo[2,3-d]pyrimidine (271-70-5)

Conditions	Yield
nickel In ammonium hydroxide for 0.5h; Heating;	69%

1,2,3,4-tetrahydronaphthalen-2 ol (530-91-6) + 4-chloro-1H-pyrrolo[2,3-d]pyrimidine (3680-69-1) → 7H-pyrrolo[2,3-d]pyrimidine (271-70-5)

Conditions	Yield
With potassium hydroxide In aqueous potassium hydroxide	65%

1,2,3,4-tetrahydro-naphthalene-2-thiol (57071-25-7) + 4-chloro-1H-pyrrolo[2,3-d]pyrimidine (3680-69-1) → 7H-pyrrolo[2,3-d]pyrimidine (271-70-5)

Conditions	Yield
In methanol; methanolic potassium hydroxide	65%

ethyl 2-cyano-4,4-diethoxybutyrate (52133-67-2) → 7H-pyrrolo[2,3-d]pyrimidine (271-70-5)

Conditions	Yield
Multi-step reaction with 5 steps 1: 64 percent / NaOEt 2: 92 percent / aq. HCl 3: 81 percent / H2 / Raney Ni 4: 66 percent / POCl3 5: 84 percent / H2 / Pd/C View Scheme

7-deazahypoxanthine (3680-71-5) → 7H-pyrrolo[2,3-d]pyrimidine (271-70-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 66 percent / POCl3 2: 84 percent / H2 / Pd/C View Scheme
Multi-step reaction with 2 steps 1: 80 percent / P4S10 / pyridine / 3 h / Heating 2: 69 percent / finely divided nickel / aq. NH3 / 0.5 h / Heating View Scheme

6-amino-5-(2,2-diethoxyethyl)-2-thioxo-2,3-dihydropyrimidin-4(1H)-one (7400-05-7) → 7H-pyrrolo[2,3-d]pyrimidine (271-70-5)

Conditions	Yield
Multi-step reaction with 4 steps 1: 92 percent / aq. HCl 2: 81 percent / H2 / Raney Ni 3: 66 percent / POCl3 4: 84 percent / H2 / Pd/C View Scheme

2-thioxo-1,2,3,7-tetrahydro-4H-pyrrolo[2,3-d]pyrimidin-4-one (67831-84-9) → 7H-pyrrolo[2,3-d]pyrimidine (271-70-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: 81 percent / H2 / Raney Ni 2: 66 percent / POCl3 3: 84 percent / H2 / Pd/C View Scheme

7H-pyrrolo[2,3-d]pyrimidine (271-70-5) → 5-Iodopyrrolo<2,3-d>pyrimidine

Conditions	Yield
With N-iodo-succinimide In acetonitrile at 20℃; for 2h;	95%
With N-iodo-succinimide In acetonitrile for 2h;	94%
With N-iodo-succinimide In acetonitrile for 3h;	85%
With potassium hydroxide; iodine In N,N-dimethyl-formamide for 2h; Ambient temperature;	70%
With potassium hydroxide; iodine In N,N-dimethyl-formamide at 20℃; for 1h;

4-(iodo)pyridin-2-amine (552331-00-7) + 7H-pyrrolo[2,3-d]pyrimidine (271-70-5) → 4-(7H-pyrrolo[2,3-d]pyrimidin-7-yl)pyridin-2-amine

Conditions	Yield
With potassium phosphate; copper(l) iodide; trans-N,N'-dimethylcyclohexane-1,2-diamine In 1,4-dioxane at 100℃; for 12h; Inert atmosphere;	93.6%

5-bromo-2-(4-methoxybenzyl)-3,7-dimethylisoindolin-1-one + 7H-pyrrolo[2,3-d]pyrimidine (271-70-5) → 2-(4-methoxybenzyl)-3,7-dimethyl-5-(7H-pyrrolo[2,3-d]pyrimidin-7-yl)isoindolin-1-one

Conditions	Yield
With potassium phosphate; copper(l) iodide; (±)-trans-1,2-diaminocyclohexane In 1,4-dioxane at 100℃; for 16h; Inert atmosphere;	93%

allyl iodid (556-56-9) + 7H-pyrrolo[2,3-d]pyrimidine (271-70-5) → 7-allyl-5-iodo-7H-pyrrolo[2,3-d]pyrimidine

Conditions	Yield
With sodium iodide In acetonitrile at 20℃; for 2h; Electrolysis; Inert atmosphere; Green chemistry;	92%

propargyl bromide (106-96-7) + 7H-pyrrolo[2,3-d]pyrimidine (271-70-5) → 7-(prop-2-yn-1-yl)-7H-pyrrolo[2,3-d]pyrimidine

Conditions	Yield
Stage #1: 7H-pyrrolo[2,3-d]pyrimidine With sodium hydride In tetrahydrofuran at 0 - 20℃; for 0.5h; Stage #2: propargyl bromide With tetra-(n-butyl)ammonium iodide In tetrahydrofuran at 0 - 20℃; for 5h;	88%

5-[(fluoromethyl)(4-nitrophenyl)-λ4-sulfanylidene]-2,2-dimethyl-1,3-dioxane-4,6-dione + 7H-pyrrolo[2,3-d]pyrimidine (271-70-5) → 7-(fluoromethyl)-7H-pyrrolo[2,3-d]pyrimidine

Conditions	Yield
Stage #1: 7H-pyrrolo[2,3-d]pyrimidine With sodium hydride In N,N-dimethyl-formamide at 30℃; for 0.25h; Schlenk technique; Stage #2: 5-[(fluoromethyl)(4-nitrophenyl)-λ4-sulfanylidene]-2,2-dimethyl-1,3-dioxane-4,6-dione In N,N-dimethyl-formamide at 30℃; for 0.166667h; Schlenk technique;	88%

1-(1-phenylvinyl)tetrahydro-1H-thiophen-1-ium tetraphenylborate + 7H-pyrrolo[2,3-d]pyrimidine (271-70-5) → 7-[(E)-styryl]pyrrolo[2,3-d]pyrimidine

Conditions	Yield
Stage #1: 1-(1-phenylvinyl)tetrahydro-1H-thiophen-1-ium tetraphenylborate; 7H-pyrrolo[2,3-d]pyrimidine In dimethyl sulfoxide at 21℃; for 0.0333333h; Schlenk technique; Stage #2: With 1,8-diazabicyclo[5.4.0]undec-7-ene In dimethyl sulfoxide at 21℃; for 12h; Schlenk technique; regioselective reaction;	82%

allyl bromide (106-95-6) + 7H-pyrrolo[2,3-d]pyrimidine (271-70-5) → 7-allyl-5-bromo-7H-pyrrolo[2,3-d]pyrimidine

Conditions	Yield
With tetrabutylammomium bromide; sodium bromide In acetonitrile at 20℃; for 2h; Electrolysis; Inert atmosphere; Green chemistry;	82%

6-chloro-N-((R)-2-fluoro-3-hydroxy-3-methylbutyl)-4-(((S)-1-fluoropropan-2-yl)amino)nicotinamide + 7H-pyrrolo[2,3-d]pyrimidine (271-70-5) → N-((R)-2-fluoro-3-hydroxy-3-methylbutyl)-4-((1-fluoropropan-2-yl)amino)-6-(7H-pyrrolo[2,3-d]pyrimidin-7-yl)nicotinamide

Conditions	Yield
With dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine; chloro[2-(dicyclohexylphosphino)-3 ,6-dimethoxy-2’,4’, 6’-triisopropyl- 1,1’-biphenyl] [2-(2-aminoethyl)phenyl]palladium(II); potassium carbonate In N,N-dimethyl acetamide; tert-butyl alcohol at 135℃; for 1h; Inert atmosphere;	81%

dimethyl 2-((fluoromethyl)(phenyl)-l4-sulfaneylidene)malonate + 7H-pyrrolo[2,3-d]pyrimidine (271-70-5) → 7-(fluoromethyl)-7H-pyrrolo[2,3-d]pyrimidine

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 40℃; for 12h; Schlenk technique; Inert atmosphere;	79%

6-chloro-4-isopropylamino-nicotinic acid ethyl ester (1011464-52-0) + 7H-pyrrolo[2,3-d]pyrimidine (271-70-5) → ethyl 4-(isopropylamino)-6-(7H-pyrrolo[2,3-d]pyrimidin-7-yl)nicotinate

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); potassium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In N,N-dimethyl acetamide at 140℃; for 1h; Inert atmosphere; Sealed tube;	77%

propane-1-sulfonic acid (2-fluoro-3-formyl-phenyl)-amide (918523-78-1) + 7H-pyrrolo[2,3-d]pyrimidine (271-70-5) → propane-1-sulfonic acid {2-fluoro-3-[hydroxy-(7H-pyrrolo[2,3-d]pyrimidin-5-yl)-methyl]-phenyl}-amide (1195070-44-0)

Conditions	Yield
With potassium hydroxide In methanol at 20℃; for 24h; Inert atmosphere;	76%

hexamethylenetetramine (100-97-0) + 7H-pyrrolo[2,3-d]pyrimidine (271-70-5) → 7H-pyrrolo[2,3-d]pyrimidine-5-carbaldehyde (1060815-89-5)

Conditions	Yield
With acetic acid In water for 8h; Inert atmosphere; Reflux;	76%
Stage #1: hexamethylenetetramine; 7H-pyrrolo[2,3-d]pyrimidine With acetic acid In water for 12h; Reflux; Stage #2: With sodium carbonate In water pH=8 - 9;

p-Chlorothiophenol (106-54-7) + 7H-pyrrolo[2,3-d]pyrimidine (271-70-5) → 5-((4-chlorophenyl)thio)-7H-pyrrolo[2,3-d]pyrimidine

Conditions	Yield
With caesium carbonate In dimethyl sulfoxide at 100℃; for 3h; Schlenk technique;	70%

ethyl 2-(6-bromo-2-(4-methoxybenzyl)-3-oxoisoindolin-1-yl)acetate + 7H-pyrrolo[2,3-d]pyrimidine (271-70-5) → ethyl 2-(2-(4-methoxybenzyl)-3-oxo-6-(7H-pyrrolo[2,3-d]pyrimidin-7-yl)isoindolin-1-yl)acetate

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane at 110℃; for 16h; Inert atmosphere;	70%

5′-bromo-7′-chloro-2′-[(4-methoxyphenyl)methyl]spiro[cyclohexane-1,3′-isoindoline]-1′-one + 7H-pyrrolo[2,3-d]pyrimidine (271-70-5) → 4′-chloro-2′-(4-methoxybenzyl)-6′-(7H-pyrrolo[2,3-d]pyrimidin-7-yl)spiro[cyclohexane-1,1′-isoindolin]-3′-one

Conditions	Yield
With potassium phosphate; copper(l) iodide; (±)-trans-1,2-diaminocyclohexane In 1,4-dioxane at 130℃; for 16h; Inert atmosphere;	64%

bis-(((isopropyl)sulfinyl)oxy)zinc + 7H-pyrrolo[2,3-d]pyrimidine (271-70-5) → 6-isopropyl-7-deazapurine (1309430-81-6)

Conditions	Yield
With tert.-butylhydroperoxide In dimethyl sulfoxide at 50℃;	62%

dichloromethane (75-09-2) + 7H-pyrrolo[2,3-d]pyrimidine (271-70-5) → 7,7'-Methylendi(7H-pyrrolo<2,3-d>pyrimidin) (87791-30-8)

Conditions	Yield
With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate In 1,2-dimethoxyethane for 3h;	55%

5-bromo-2-[(4-methoxyphenyl)methyl]isoindolin-1-one + 7H-pyrrolo[2,3-d]pyrimidine (271-70-5) → 2-(4-methoxybenzyl)-5-(7H-pyrrolo[2,3-d]pyrimidin-7-yl)isoindolin-1-one

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); potassium tert-butylate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane at 100℃; for 12h; Temperature; Inert atmosphere;	54%

7H-pyrrolo[2,3-d]pyrimidine (271-70-5) + methyl iodide (74-88-4) → 7-Methyl-7H-pyrrolo<2,3-d>pyrimidin (87791-29-5)

Conditions	Yield
With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate In 1,2-dimethoxyethane; dichloromethane	53%

5-bromo-7-fluoro-2-(4-methoxybenzyl)isoindolin-1-one + 7H-pyrrolo[2,3-d]pyrimidine (271-70-5) → 7-fluoro-2-(4-methoxybenzyl)-5-(7H-pyrrolo[2,3-d]pyrimidin-7-yl)isoindolin-1-one

Conditions	Yield
With potassium phosphate; copper(l) iodide; (±)-trans-1,2-diaminocyclohexane In 1,4-dioxane at 100℃; for 16h; Inert atmosphere;	51%

propynoic acid methyl ester (922-67-8) + 7H-pyrrolo[2,3-d]pyrimidine (271-70-5) → methyl 2-(7H-pyrrolo[2,3-d]pyrimidin-7-yl)acrylate

Conditions	Yield
With sodium acetate; acetic acid; triphenylphosphine In toluene at 110℃; for 24h; Inert atmosphere; Schlenk technique;	51%

5-bromo-2-(4-methoxybenzyl)-3-methylisoindolin-1-one + 7H-pyrrolo[2,3-d]pyrimidine (271-70-5) → 2-(4-methoxybenzyl)-3-methyl-5-(7H-pyrrolo[2,3-d]pyrimidin-7-yl)isoindolin-1-one

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); potassium tert-butylate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane at 95℃; for 12h; Inert atmosphere;	45%

N-(2-fluoro-3-formyl-phenyl)-4-trifluoromethyl-benzenesulfonamide + 7H-pyrrolo[2,3-d]pyrimidine (271-70-5) → N-{2-fluoro-3-[hydroxy-(7H-pyrrolo[2,3-d]pyrimidin-5-yl)-methyl]-phenyl}-4-trifluoromethyl-benzenesulfonamide (1195071-03-4)

Conditions	Yield
With potassium hydroxide In methanol at 20℃; for 24h; Inert atmosphere;	44%

cyclohexane (110-82-7) + 7H-pyrrolo[2,3-d]pyrimidine (271-70-5) → C12H15N3 + 2,4-dicyclohexyl-7H-pyrrolo[2,3-d]pyrimidine

Conditions	Yield
With hydrogenchloride; dihydrogen peroxide In water; acetonitrile at 20℃; for 18h; Minisci Aromatic Substitution; Inert atmosphere; Irradiation; Green chemistry;	A 44% B 17%

Upstream product

• 1421-27-8 3,7-Dihydro-4H-pyrrolo<2,3-d>pyrimidin-4-thion 
• 3680-69-1 4-chloro-1H-pyrrolo[2,3-d]pyrimidine 
• 530-91-6 1,2,3,4-tetrahydronaphthalen-2 ol 
• 57071-25-7 1,2,3,4-tetrahydro-naphthalene-2-thiol 
• 67831-84-9 2-thioxo-1,2,3,7-tetrahydro-4H-pyrrolo[2,3-d]pyrimidin-4-one 
• 7400-05-7 6-amino-5-(2,2-diethoxyethyl)-2-thioxo-2,3-dihydropyrimidin-4(1H)-one 
• 3680-71-5 7-deazahypoxanthine 
• 52133-67-2 ethyl 2-cyano-4,4-diethoxybutyrate 

Downstream Products

• 1195070-44-0 propane-1-sulfonic acid {2-fluoro-3-[hydroxy-(7H-pyrrolo[2,3-d]pyrimidin-5-yl)-methyl]-phenyl}-amide 
• 1195070-37-1 propane-1-sulfonic acid {2,4-difluoro-3-[hydroxy-(7H-pyrrolo[2,3-d]pyrimidin-5-yl)-methyl]-phenyl}-amide 
• 1195071-03-4 N-{2-fluoro-3-[hydroxy-(7H-pyrrolo[2,3-d]pyrimidin-5-yl)-methyl]-phenyl}-4-trifluoromethyl-benzenesulfonamide 
• 1318945-74-2 {2,4-difluoro-3-[hydroxy-(7H-pyrrolo[2,3-d]pyrimidin-5-yl)-methyl]-phenyl}-carbamic acid methyl ester 
• 1227957-99-4 {2,4-difluoro-3-[hydroxy-(7H-pyrrolo[2,3-d]pyrimidin-5-yl)-methyl]-phenyl}-carbamic acid benzyl ester 
• 1195070-40-6 N-2,4-difluoro-3-[hydroxy-(7H-pyrrolo[2,3-d]pyrimidin-5-yl)-methyl]-phenyl-4-trifluoromethyl-benzenesulfonamide 
• 1309430-81-6 6-isopropyl-7-deazapurine 

Relevant academic research and scientific papers

AZAINDOLE DERIVATIVE

The present invention provides a (di)azaindole derivative represented by the formula (I). A compound of the present invention inhibits a Cdc7 protein kinase activity and suppresses cell proliferation.

AZAINDOLE DERIVATIVES WITH A COMBINATION OF PARTIAL NICOTINIC ACETYL-CHOLINE RECEPTOR AGONISM AND DOPAMINE REUPTAKE INHIBITION

Azaindole derivatives of formula (I): wherein the symbols have the meanings given in the specification, are described. These compounds have a combination of partial nicotinic acetylcholine receptor agonism and dopamine reuptake inhibition. The invention also relates to pharmaceutical compositions containing these compounds, to methods for preparing them, methods for preparing novel intermediates useful for their synthesis, methods for preparing compositions, and uses of such compounds and compositions, for example, their use in administering them to patients to achieve a therapeutic effect in disorders in which nicotinic receptors and/or dopamine transporters are involved, or that can be treated via manipulation of those receptors

Xanthine oxidase-activated prodrugs of thymidine phosphorylase inhibitors

Thymidine phosphorylase (TP) is over-expressed in various tumour types and plays an important role in tumour angiogenesis, growth, invasion and metastasis. The enzymatic activity of TP is required for the angiogenic effect of TP, therefore, inhibitors of TP are of significant interest in cancer chemotherapy. A series of xanthine oxidase (XO) activated prodrugs of known inhibitors of TP have been designed and synthesized with the ultimate intent of improving tumour selectivity and pharmacokinetic characteristics. These prodrugs were not inhibitors of TP, but were selectively oxidized by XO at C-2 and/or C-4 of the uracil ring moiety to generate the desired TP inhibitor. Molecular modelling of both the TP inhibitors and XO-activated prodrugs rationalized their binding in the active site of the human TP crystal structure.

DEAZAPURINES USEFUL AS INHIBITORS OF JANUS KINASES

The present invention relates to compounds useful as inhibitors of protein kinases, particularly of JAK family kinases. The invention also provides pharmaceutically acceptable compositions comprising said compounds and methods of using the compositions in the treatment of various disease, conditions, or disorders.

Synthesis and enzymatic evaluation of xanthine oxidase-activated prodrugs based on inhibitors of thymidine phosphorylase

A series of xanthine oxidase-activated prodrugs of known inhibitors of thymidine phosphorylase are described. These prodrugs were oxidised by xanthine oxidase at C-2 and/or C-4 of the uracil ring to generate the desired TP inhibitor. The scheme shows the prodrug of TPI. A series of xanthine oxidase-activated prodrugs of known inhibitors of thymidine phosphorylase has been designed and synthesised to introduce tumour selectivity. These prodrugs were oxidised by xanthine oxidase at C-2 and/or C-4 of the uracil ring to generate the desired TP inhibitor.

Substituted pyrrolopyrimidines and processes for their preparation

There are described 7H-pyrrolo[2,3-d]pyrimidine derivatives of the formula I in which the substituents are as defined in claim 1. These compounds inhibit the tyrosine kinase activity of the receptor for the epidermal growth factor (EGF) and c-erbB2 kinase and can be used as anti-tumor agents.

Condensed heteroaromatic ring systems. XXI. Synthesis of pyrrolo[2,3-d]pyrimidines and pyrrolo[3,2-d]pyrimidines

Pyrrolo[2,3-d]pyrimidines and pyrrolo[3,2-d]pyrimidines were synthesized in high yields by the palladium-catalyzed reaction of 4-acetylamino-5-bromopyrimidines and 5-acetylamino-4-iodopyrimidines with (Z)-1-ethoxy-2-(tributylstannyl)ethene followed by cyclization under acidic conditions.

ara-7-Deazanebularine - Synthesis of a Fluorescent Pyrrolopyrimidine Nucleoside by Phase-Transfer Glycosylation

ara-7-Deazanebularine (2b) and its 6-methylthio derivative 2a have been synthesized via phase-transfer glycosylation of 4-methylthio-7H-pyrrolopyrimidine (4a) with 1-bromo-2,3,5-tri-O-benzyl-D-arabinofuranose (7).Omitting the halogenose and carrying out the reaction of 4a or 4b in dichloromethane leads to the methylene-bridged chromophores 6a and 6b, respectively.In contrast to pyrrolopyrimidines with substituents in position 2 and 4 compound 4a is glycosylated at N-7 and N-1.The formation of anomers and isomers is influenced by the phase-transfer catalyst.The N-1glycosylated 10 is sensitive against hydrolysis at the N-glycosylic bond which is not found for the N-7 isomer 8a.Debenzylation of the methylthio nucleosides 8a or 9a is accomplished using boron trichloride.Raney nickel catalyst removes the sulfur yielding the title compound 2b which exhibits strong fluorescence.