271-70-5

Basic information

• Product Name: DEAZAPURINE
• Synonyms: 7H-PYRROLO[2,3-D]PYRIMIDINE;DEAZAPURINE;1H-Pyrrolo[2,3-d]pyrimidine (8CI,9CI);3H-Pyrrolo[2,3-d]pyrimidine;NSC 94210;1H-Pyrrolo[2,3-d]pyrimidine;7-Deazapurine;1H-Pyrrolo[2,3-d]pyrimidi...
• CAS NO: 271-70-5
• Molecular Formula: C₆H₅N₃
• Molecular Weight: 119.12
• Product Categories: Heterocycle-Pyrimidine series;PYRIMIDINE
• Mol File: 271-70-5.mol
• Article Data: 9

Chemical Properties

• Melting Point: 133℃
• Boiling Point: 288.3 °C at 760 mmHg
• Flash Point: 141.8 °C
• Appearance: /
• Density: 1.38
• Vapor Pressure: 0.00409mmHg at 25°C
• Refractive Index: 1.715
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: Chloroform, Dichloromethane, DMSO, Methanol
• PKA: 12.79±0.20(Predicted)
• CAS DataBase Reference: DEAZAPURINE(CAS DataBase Reference)
• NIST Chemistry Reference: DEAZAPURINE(271-70-5)
• EPA Substance Registry System: DEAZAPURINE(271-70-5)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 271-70-5(Hazardous Substances Data)

Usage

General Description

Deazapurine is a class of chemical compounds derived from purine, a heterocyclic aromatic organic compound vital in molecular biology. The name deazapurine is applied because it is structurally similar to purine, but with a nitrogen atom replaced by a carbon atom. Deazapurines perform critical roles in nucleic acids, coenzymes, and high-energy compounds. They encompass several biologically significant molecules, such as antibiotics (tubercidin and toyocamycin), cofactors (coenzyme F420), and components of tRNAs, and have functions that impact almost every aspect of cellular metabolism.

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

• 57071-25-7 1,2,3,4-tetrahydro-naphthalene-2-thiol 
• 3680-69-1 4-chloro-1H-pyrrolo[2,3-d]pyrimidine 
• 530-91-6 1,2,3,4-tetrahydronaphthalen-2 ol 
• 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 
• 1421-27-8 3,7-Dihydro-4H-pyrrolo<2,3-d>pyrimidin-4-thion 

Downstream Products

• 175791-49-8 5-Bromopyrrolo<2,3-d>pyrimidine 
• 175791-53-4 5-Iodopyrrolo<2,3-d>pyrimidine 
• 1168106-39-5 4-phenyl-7H-pyrrolo[2,3-d]pyrimidine 
• 945950-37-8 4-methyl-7H-pyrrazolo[2,3-d]pyrimidine 
• 63205-44-7 6-ethyl-7-deazapurine 
• 1607005-13-9 4-(4-methylphenyl)-7H-pyrrolo[2,3-d]pyrimidine 

Relevant articles and documents

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.

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.

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.