1H-Pyrrolo[2,3-d]pyrimidine supplier

Name
DEAZAPURINE
EINECS
CAS No. 271-70-5
Article Data13
CAS DataBase
Density 1.348 g/cm³
Solubility
Melting Point 133 °C
Formula C₆H₅N₃
Boiling Point 288.3 °C at 760 mmHg
Molecular Weight 119.126
Flash Point 141.8 °C
Transport Information
Appearance
Safety
Risk Codes 22
Molecular Structure
Hazard Symbols Xn
Synonyms 1H-Pyrrolo[2,3-d]pyrimidine(8CI,9CI);3H-Pyrrolo[2,3-d]pyrimidine;7-Deazapurine;NSC 94210;7H-Pyrrolo[2,3-d]pyrimidine;
PSA 41.57000
LogP 0.95790

Synthetic route

: 3680-69-1
4-chloro-1H-pyrrolo[2,3-d]pyrimidine

: 271-70-5
7H-pyrrolo[2,3-d]pyrimidine

Conditions

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

: 271-70-5
7H-pyrrolo[2,3-d]pyrimidine

Conditions

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

: 1421-27-8
3,7-Dihydro-4H-pyrrolo<2,3-d>pyrimidin-4-thion

: 271-70-5
7H-pyrrolo[2,3-d]pyrimidine

Conditions

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

: 530-91-6
1,2,3,4-tetrahydronaphthalen-2 ol

: 3680-69-1
4-chloro-1H-pyrrolo[2,3-d]pyrimidine

: 271-70-5
7H-pyrrolo[2,3-d]pyrimidine

Conditions

Conditions	Yield
With potassium hydroxide In aqueous potassium hydroxide	65%

: 57071-25-7
1,2,3,4-tetrahydro-naphthalene-2-thiol

: 3680-69-1
4-chloro-1H-pyrrolo[2,3-d]pyrimidine

: 271-70-5
7H-pyrrolo[2,3-d]pyrimidine

Conditions

Conditions	Yield
In methanol; methanolic potassium hydroxide	65%

: 52133-67-2
ethyl 2-cyano-4,4-diethoxybutyrate

: 271-70-5
7H-pyrrolo[2,3-d]pyrimidine

Conditions

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

: 3680-71-5
7-deazahypoxanthine

: 271-70-5
7H-pyrrolo[2,3-d]pyrimidine

Conditions

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

: 7400-05-7
6-amino-5-(2,2-diethoxyethyl)-2-thioxo-2,3-dihydropyrimidin-4(1H)-one

: 271-70-5
7H-pyrrolo[2,3-d]pyrimidine

Conditions

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

: 67831-84-9
2-thioxo-1,2,3,7-tetrahydro-4H-pyrrolo[2,3-d]pyrimidin-4-one

: 271-70-5
7H-pyrrolo[2,3-d]pyrimidine

Conditions

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

: 271-70-5
7H-pyrrolo[2,3-d]pyrimidine

: 5-Iodopyrrolo<2,3-d>pyrimidine

Conditions

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;

: 552331-00-7
4-(iodo)pyridin-2-amine

: 271-70-5
7H-pyrrolo[2,3-d]pyrimidine

: 4-(7H-pyrrolo[2,3-d]pyrimidin-7-yl)pyridin-2-amine

Conditions

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

: 271-70-5
7H-pyrrolo[2,3-d]pyrimidine

: 2-(4-methoxybenzyl)-3,7-dimethyl-5-(7H-pyrrolo[2,3-d]pyrimidin-7-yl)isoindolin-1-one

Conditions

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

: 556-56-9
allyl iodid

: 271-70-5
7H-pyrrolo[2,3-d]pyrimidine

: 7-allyl-5-iodo-7H-pyrrolo[2,3-d]pyrimidine

Conditions

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

: 106-96-7
propargyl bromide

: 271-70-5
7H-pyrrolo[2,3-d]pyrimidine

: 7-(prop-2-yn-1-yl)-7H-pyrrolo[2,3-d]pyrimidine

Conditions

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

: 271-70-5
7H-pyrrolo[2,3-d]pyrimidine

: 7-(fluoromethyl)-7H-pyrrolo[2,3-d]pyrimidine

Conditions

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

: 271-70-5
7H-pyrrolo[2,3-d]pyrimidine

: 7-[(E)-styryl]pyrrolo[2,3-d]pyrimidine

Conditions

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%

: 106-95-6
allyl bromide

: 271-70-5
7H-pyrrolo[2,3-d]pyrimidine

: 7-allyl-5-bromo-7H-pyrrolo[2,3-d]pyrimidine

Conditions

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

: 271-70-5
7H-pyrrolo[2,3-d]pyrimidine

: 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

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

: 271-70-5
7H-pyrrolo[2,3-d]pyrimidine

: 7-(fluoromethyl)-7H-pyrrolo[2,3-d]pyrimidine

Conditions

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

: 1011464-52-0
6-chloro-4-isopropylamino-nicotinic acid ethyl ester

: 271-70-5
7H-pyrrolo[2,3-d]pyrimidine

: ethyl 4-(isopropylamino)-6-(7H-pyrrolo[2,3-d]pyrimidin-7-yl)nicotinate

Conditions

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%

: 918523-78-1
propane-1-sulfonic acid (2-fluoro-3-formyl-phenyl)-amide

: 271-70-5
7H-pyrrolo[2,3-d]pyrimidine

: 1195070-44-0
propane-1-sulfonic acid {2-fluoro-3-[hydroxy-(7H-pyrrolo[2,3-d]pyrimidin-5-yl)-methyl]-phenyl}-amide

Conditions

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

: 100-97-0
hexamethylenetetramine

: 271-70-5
7H-pyrrolo[2,3-d]pyrimidine

: 1060815-89-5
7H-pyrrolo[2,3-d]pyrimidine-5-carbaldehyde

Conditions

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;

: 106-54-7
p-Chlorothiophenol

: 271-70-5
7H-pyrrolo[2,3-d]pyrimidine

: 5-((4-chlorophenyl)thio)-7H-pyrrolo[2,3-d]pyrimidine

Conditions

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

: 271-70-5
7H-pyrrolo[2,3-d]pyrimidine

: ethyl 2-(2-(4-methoxybenzyl)-3-oxo-6-(7H-pyrrolo[2,3-d]pyrimidin-7-yl)isoindolin-1-yl)acetate

Conditions

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

: 271-70-5
7H-pyrrolo[2,3-d]pyrimidine

: 4′-chloro-2′-(4-methoxybenzyl)-6′-(7H-pyrrolo[2,3-d]pyrimidin-7-yl)spiro[cyclohexane-1,1′-isoindolin]-3′-one

Conditions

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

: 271-70-5
7H-pyrrolo[2,3-d]pyrimidine

: 1309430-81-6
6-isopropyl-7-deazapurine

Conditions

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

: 75-09-2
dichloromethane

: 271-70-5
7H-pyrrolo[2,3-d]pyrimidine

: 87791-30-8
7,7'-Methylendi(7H-pyrrolo<2,3-d>pyrimidin)

Conditions

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

: 271-70-5
7H-pyrrolo[2,3-d]pyrimidine

: 2-(4-methoxybenzyl)-5-(7H-pyrrolo[2,3-d]pyrimidin-7-yl)isoindolin-1-one

Conditions

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%

: 271-70-5
7H-pyrrolo[2,3-d]pyrimidine

: 74-88-4
methyl iodide

: 87791-29-5
7-Methyl-7H-pyrrolo<2,3-d>pyrimidin

Conditions

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

: 271-70-5
7H-pyrrolo[2,3-d]pyrimidine

: 7-fluoro-2-(4-methoxybenzyl)-5-(7H-pyrrolo[2,3-d]pyrimidin-7-yl)isoindolin-1-one

Conditions

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

: 922-67-8
propynoic acid methyl ester

: 271-70-5
7H-pyrrolo[2,3-d]pyrimidine

: methyl 2-(7H-pyrrolo[2,3-d]pyrimidin-7-yl)acrylate

Conditions

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

: 271-70-5
7H-pyrrolo[2,3-d]pyrimidine

: 2-(4-methoxybenzyl)-3-methyl-5-(7H-pyrrolo[2,3-d]pyrimidin-7-yl)isoindolin-1-one

Conditions

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

: 271-70-5
7H-pyrrolo[2,3-d]pyrimidine

: 1195071-03-4
N-{2-fluoro-3-[hydroxy-(7H-pyrrolo[2,3-d]pyrimidin-5-yl)-methyl]-phenyl}-4-trifluoromethyl-benzenesulfonamide

Conditions

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

: 110-82-7
cyclohexane

: 271-70-5
7H-pyrrolo[2,3-d]pyrimidine

A: C12H15N3

B: 2,4-dicyclohexyl-7H-pyrrolo[2,3-d]pyrimidine

Conditions

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%

...Expand

1H-Pyrrolo[2,3-d]pyrimidine Specification

The cas register number of 1H-Pyrrolo[2,3-d]pyrimidine is 271-70-5. It also can be called as 3H-Pyrrolo[2,3-d]pyrimidine and the IUPAC Name about this chemical is 7H-pyrrolo[2,3-d]pyrimidine. It belongs to the Pyrimidine.

Physical properties about 1H-Pyrrolo[2,3-d]pyrimidine are: (1)ACD/LogP: -0.42; (2)ACD/LogD (pH 5.5): -0.43; (3)ACD/LogD (pH 7.4): -0.42; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 13.82; (7)ACD/KOC (pH 7.4): 14.09; (8)#H bond acceptors: 3; (9)#H bond donors: 1; (10)Polar Surface Area: 30.71Å²; (11)Index of Refraction: 1.715; (12)Molar Refractivity: 34.71 cm³; (13)Molar Volume: 88.3 cm³; (14)Polarizability: 13.76x10^-24cm³; (15)Surface Tension: 73.9 dyne/cm; (16)Enthalpy of Vaporization: 50.64 kJ/mol; (17)Boiling Point: 288.3 °C at 760 mmHg; (18)Vapour Pressure: 0.00409 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: n1cc2c(nc1)ncc2
(2)InChI: InChI=1/C6H5N3/c1-2-8-6-5(1)3-7-4-9-6/h1-4H,(H,7,8,9)
(3)InChIKey: JJTNLWSCFYERCK-UHFFFAOYAC
(4)Std. InChI: InChI=1S/C6H5N3/c1-2-8-6-5(1)3-7-4-9-6/h1-4H,(H,7,8,9)
(5)Std. InChIKey: JJTNLWSCFYERCK-UHFFFAOYSA-N

Product Name

DEAZAPURINE

Synthetic route

1H-Pyrrolo[2,3-d]pyrimidine Specification

Related Products

Hot Products