8-Bromo-7-(2-butyn-1-yl)-3,7-dihydro-3-methyl-1-[(4-methyl-2-quinazolinyl)methyl]-1H-purine-2,6-dione supplier

Name
8-Bromo-7-but-2-ynyl-3-methyl-1-(4-methyl-quinazolin-2-ylmethyl)-3,7-dihydro-purine-2,6-dione
EINECS 922-028-0
CAS No. 853029-57-9
Article Data37
CAS DataBase
Density 1.6±0.1 g/cm³
Solubility
Melting Point
Formula C₂₀H₁₇BrN₆O₂
Boiling Point 558.8±60.0 °C at 760 mmHg
Molecular Weight 453.298
Flash Point 291.8±32.9 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 1-[(4-Methylquinazolin-2-yl)methyl]-3-methyl-7-(2-butyn-1-yl)-8-bromoxanthine;
PSA 87.60000
LogP 1.98240

Synthetic route

: 666816-98-4
8-bromo-7-(but-2-yn-1-yl)-3-methyl-2,,6-dihydro-1H-purine-2,6-dione

: 109113-72-6
2-chloromethyl-4-methylquinazoline

: 853029-57-9
2-bromo-1-(but-2-ynyl)-4-methyl-6-((4-methylquinazolin-2-yl)methyl)-1H-imidazo[4,5-b]pyridine-5,7-(4H,6H)-dione

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 8h;	95.77%
With potassium carbonate In 1-methyl-pyrrolidin-2-one at 75℃; for 6h;	93%
With sodium carbonate In N,N-dimethyl acetamide at 100℃; for 6h; Temperature; Large scale;	89.4%

: N-(2-acetylphenyl)-2-[8-bromo-7-(but-2-yn-1-yl)-3-methyl -2,6-dioxo-2,3,6,7-tetrahydro- 1H-purin-1-yl]acetamide

: 853029-57-9
2-bromo-1-(but-2-ynyl)-4-methyl-6-((4-methylquinazolin-2-yl)methyl)-1H-imidazo[4,5-b]pyridine-5,7-(4H,6H)-dione

Conditions

Conditions	Yield
With ammonium acetate; acetic acid at 95 - 100℃; Inert atmosphere;	95%

: 666816-98-4
8-bromo-7-(but-2-yn-1-yl)-3-methyl-2,,6-dihydro-1H-purine-2,6-dione

: 2-p-toluenesulfonylmethyl-4-methylquinazoline

: 853029-57-9
2-bromo-1-(but-2-ynyl)-4-methyl-6-((4-methylquinazolin-2-yl)methyl)-1H-imidazo[4,5-b]pyridine-5,7-(4H,6H)-dione

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 6h;	93%

: 666816-98-4
8-bromo-7-(but-2-yn-1-yl)-3-methyl-2,,6-dihydro-1H-purine-2,6-dione

: 4-chloromethyl-2-methylquinazoline

: 853029-57-9
2-bromo-1-(but-2-ynyl)-4-methyl-6-((4-methylquinazolin-2-yl)methyl)-1H-imidazo[4,5-b]pyridine-5,7-(4H,6H)-dione

Conditions

Conditions	Yield
With potassium carbonate; potassium iodide In 1-methyl-pyrrolidin-2-one at 75℃; for 3h; Temperature; Large scale;	90%

: C16H13BrN6O2

: 3355-28-0
1-Bromo-2-butyne

: 853029-57-9
2-bromo-1-(but-2-ynyl)-4-methyl-6-((4-methylquinazolin-2-yl)methyl)-1H-imidazo[4,5-b]pyridine-5,7-(4H,6H)-dione

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 50℃; for 3h;	86.3%

: 666816-98-4
8-bromo-7-(but-2-yn-1-yl)-3-methyl-2,,6-dihydro-1H-purine-2,6-dione

: 2-(1-bromomethyl)-4-methylquinazoline

: 853029-57-9
2-bromo-1-(but-2-ynyl)-4-methyl-6-((4-methylquinazolin-2-yl)methyl)-1H-imidazo[4,5-b]pyridine-5,7-(4H,6H)-dione

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 7h;	82%
With sodium carbonate In 1-methyl-pyrrolidin-2-one at 100 - 120℃;	72%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 8h;
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 8h;
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 8h;

: 666816-98-4
8-bromo-7-(but-2-yn-1-yl)-3-methyl-2,,6-dihydro-1H-purine-2,6-dione

2-halogenomethyl-4-methyl-quinazoline: 2-halogenomethyl-4-methyl-quinazoline

: 853029-57-9
2-bromo-1-(but-2-ynyl)-4-methyl-6-((4-methylquinazolin-2-yl)methyl)-1H-imidazo[4,5-b]pyridine-5,7-(4H,6H)-dione

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 6h;

: 93703-24-3
3-methyl-8-bromoxanthine

: 853029-57-9
2-bromo-1-(but-2-ynyl)-4-methyl-6-((4-methylquinazolin-2-yl)methyl)-1H-imidazo[4,5-b]pyridine-5,7-(4H,6H)-dione

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 - 30 °C 1.2: 25 - 30 °C 2.1: tetrabutylammomium bromide; potassium carbonate / dimethyl sulfoxide / 75 - 80 °C View Scheme
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C 2: sodium carbonate / N,N-dimethyl-formamide / 12 h / 80 °C View Scheme
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 4 h / 80 °C 2: potassium carbonate / N,N-dimethyl-formamide / 6 h / 65 °C View Scheme

: 1076-22-8
3-methylxanthine

: 853029-57-9
2-bromo-1-(but-2-ynyl)-4-methyl-6-((4-methylquinazolin-2-yl)methyl)-1H-imidazo[4,5-b]pyridine-5,7-(4H,6H)-dione

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium acetate / acetic acid / 25 - 30 °C 1.2: 10 - 65 °C 2.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 - 30 °C 2.2: 25 - 30 °C 3.1: tetrabutylammomium bromide; potassium carbonate / dimethyl sulfoxide / 75 - 80 °C View Scheme
Multi-step reaction with 3 steps 1: sodium acetate; acetic acid; bromine / 2 h / 65 °C 2: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 4 h / 80 °C 3: potassium carbonate / N,N-dimethyl-formamide / 6 h / 65 °C View Scheme
Multi-step reaction with 3 steps 1: acetic acid; sodium acetate; bromine / 2 h / 65 °C 2: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 12 h / 20 °C 3: potassium carbonate / N,N-dimethyl acetamide / 75 - 95 °C View Scheme
Multi-step reaction with 3 steps 1.1: acetic acid; sodium acetate / 25 - 30 °C 1.2: 10 - 65 °C 2.1: N-ethyl-N,N-diisopropylamine / acetone / Reflux 3.1: potassium carbonate; tetrabutylammomium bromide / dimethyl sulfoxide / 20 - 80 °C View Scheme
Multi-step reaction with 3 steps 1: sodium acetate; acetic acid; bromine / 3 h / 65 °C 2: triethylamine / N,N-dimethyl-formamide / 10 h / 20 °C 3: potassium carbonate / N,N-dimethyl-formamide / 8 h / 90 °C View Scheme

: 551-93-9
2-aminoacetophenone

: 853029-57-9
2-bromo-1-(but-2-ynyl)-4-methyl-6-((4-methylquinazolin-2-yl)methyl)-1H-imidazo[4,5-b]pyridine-5,7-(4H,6H)-dione

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: hydrogenchloride / 1,4-dioxane / 10 °C / Cooling 1.2: 1 h / -10 °C 2.1: potassium carbonate / N,N-dimethyl-formamide / 6 h / 65 °C View Scheme
Multi-step reaction with 2 steps 1: hydrogenchloride / 1,4-dioxane / 2 h / 6 °C 2: sodium carbonate / 1-methyl-pyrrolidin-2-one / 2 h / 140 °C View Scheme
Multi-step reaction with 2 steps 1: copper(l) chloride; oxygen; potassium carbonate / tetrahydrofuran / 12 h / Reflux 2: potassium carbonate / N,N-dimethyl-formamide / 6 h / 80 °C View Scheme

: 666816-98-4
8-bromo-7-(but-2-yn-1-yl)-3-methyl-2,,6-dihydro-1H-purine-2,6-dione

: 2-(2-bromoethyl)-4-methylquinazoline

: 853029-57-9
2-bromo-1-(but-2-ynyl)-4-methyl-6-((4-methylquinazolin-2-yl)methyl)-1H-imidazo[4,5-b]pyridine-5,7-(4H,6H)-dione

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl acetamide at 20℃; for 8h;

: 6140-11-0
N-(2-acetylphenyl)-2-chloroacetamide

: 853029-57-9
2-bromo-1-(but-2-ynyl)-4-methyl-6-((4-methylquinazolin-2-yl)methyl)-1H-imidazo[4,5-b]pyridine-5,7-(4H,6H)-dione

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium iodide; potassium carbonate / dimethyl sulfoxide / 50 - 55 °C / Inert atmosphere 2: ammonium acetate; acetic acid / 95 - 100 °C / Inert atmosphere View Scheme

: 1005482-51-8
8-bromo-3-methyl-7-(thietan-3-yl)-3,7-dihydro-1H-pyrine-2,6-dione

: 853029-57-9
2-bromo-1-(but-2-ynyl)-4-methyl-6-((4-methylquinazolin-2-yl)methyl)-1H-imidazo[4,5-b]pyridine-5,7-(4H,6H)-dione

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: potassium hydroxide / N,N-dimethyl-formamide; water / 0.5 h 1.2: 6 h / 20 °C 2.1: acetic acid; dihydrogen peroxide / 0.5 h / Reflux 3.1: sodium ethanolate; ethanol / 1 h / Reflux; Inert atmosphere 4.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 3 h / 50 °C View Scheme

: C19H17BrN6O2S

: 853029-57-9
2-bromo-1-(but-2-ynyl)-4-methyl-6-((4-methylquinazolin-2-yl)methyl)-1H-imidazo[4,5-b]pyridine-5,7-(4H,6H)-dione

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: acetic acid; dihydrogen peroxide / 0.5 h / Reflux 2: sodium ethanolate; ethanol / 1 h / Reflux; Inert atmosphere 3: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 3 h / 50 °C View Scheme

: C19H17BrN6O4S

: 853029-57-9
2-bromo-1-(but-2-ynyl)-4-methyl-6-((4-methylquinazolin-2-yl)methyl)-1H-imidazo[4,5-b]pyridine-5,7-(4H,6H)-dione

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium ethanolate; ethanol / 1 h / Reflux; Inert atmosphere 2: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 3 h / 50 °C View Scheme

: 666816-98-4
8-bromo-7-(but-2-yn-1-yl)-3-methyl-2,,6-dihydro-1H-purine-2,6-dione

: 109113-72-6
2-chloromethyl-4-methylquinazoline

A: 853029-57-9
2-bromo-1-(but-2-ynyl)-4-methyl-6-((4-methylquinazolin-2-yl)methyl)-1H-imidazo[4,5-b]pyridine-5,7-(4H,6H)-dione

B: C40H34Br2N12O4

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl acetamide at 75 - 85℃;	A n/a B 2 g

...Expand

: 2434-53-9
6-amino-1-methyluracil

: 853029-57-9
2-bromo-1-(but-2-ynyl)-4-methyl-6-((4-methylquinazolin-2-yl)methyl)-1H-imidazo[4,5-b]pyridine-5,7-(4H,6H)-dione

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1.1: acetic acid; sodium nitrite / water / 1 h / 50 °C 2.1: ammonium hydroxide; sodium dithionite / 1 h / 35 - 60 °C 3.1: water / 3 h / 105 °C 3.2: 1 h / 105 °C 4.1: acetic acid; sodium acetate; bromine / 2 h / 65 °C 5.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 12 h / 20 °C 6.1: potassium carbonate / N,N-dimethyl acetamide / 75 - 95 °C View Scheme
Multi-step reaction with 6 steps 1.1: acetic acid; sodium nitrite / water / 1 h / 50 °C 2.1: sodium dithionite; ammonia / 1 h / 50 °C 3.1: water / 3 h / Reflux; Inert atmosphere 4.1: acetic acid; sodium acetate / 25 - 30 °C 4.2: 10 - 65 °C 5.1: N-ethyl-N,N-diisopropylamine / acetone / Reflux 6.1: potassium carbonate; tetrabutylammomium bromide / dimethyl sulfoxide / 20 - 80 °C View Scheme

Yield

Multi-step reaction with 6 steps
1.1: acetic acid; sodium nitrite / water / 1 h / 50 °C
2.1: ammonium hydroxide; sodium dithionite / 1 h / 35 - 60 °C
3.1: water / 3 h / 105 °C
3.2: 1 h / 105 °C
4.1: acetic acid; sodium acetate; bromine / 2 h / 65 °C
5.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 12 h / 20 °C
6.1: potassium carbonate / N,N-dimethyl acetamide / 75 - 95 °C
View Scheme

Multi-step reaction with 6 steps
1.1: acetic acid; sodium nitrite / water / 1 h / 50 °C
2.1: sodium dithionite; ammonia / 1 h / 50 °C
3.1: water / 3 h / Reflux; Inert atmosphere
4.1: acetic acid; sodium acetate / 25 - 30 °C
4.2: 10 - 65 °C
5.1: N-ethyl-N,N-diisopropylamine / acetone / Reflux
6.1: potassium carbonate; tetrabutylammomium bromide / dimethyl sulfoxide / 20 - 80 °C
View Scheme

: 6972-78-7
6-amino-1-methyl-5-nitrosouracil

: 853029-57-9
2-bromo-1-(but-2-ynyl)-4-methyl-6-((4-methylquinazolin-2-yl)methyl)-1H-imidazo[4,5-b]pyridine-5,7-(4H,6H)-dione

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: ammonium hydroxide; sodium dithionite / 1 h / 35 - 60 °C 2.1: water / 3 h / 105 °C 2.2: 1 h / 105 °C 3.1: acetic acid; sodium acetate; bromine / 2 h / 65 °C 4.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 12 h / 20 °C 5.1: potassium carbonate / N,N-dimethyl acetamide / 75 - 95 °C View Scheme
Multi-step reaction with 5 steps 1.1: sodium dithionite; ammonia / 1 h / 50 °C 2.1: water / 3 h / Reflux; Inert atmosphere 3.1: acetic acid; sodium acetate / 25 - 30 °C 3.2: 10 - 65 °C 4.1: N-ethyl-N,N-diisopropylamine / acetone / Reflux 5.1: potassium carbonate; tetrabutylammomium bromide / dimethyl sulfoxide / 20 - 80 °C View Scheme

: 6972-82-3
5,6-diamino-1-methyluracil

: 853029-57-9
2-bromo-1-(but-2-ynyl)-4-methyl-6-((4-methylquinazolin-2-yl)methyl)-1H-imidazo[4,5-b]pyridine-5,7-(4H,6H)-dione

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: water / 3 h / 105 °C 1.2: 1 h / 105 °C 2.1: acetic acid; sodium acetate; bromine / 2 h / 65 °C 3.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 12 h / 20 °C 4.1: potassium carbonate / N,N-dimethyl acetamide / 75 - 95 °C View Scheme
Multi-step reaction with 4 steps 1.1: water / 3 h / Reflux; Inert atmosphere 2.1: acetic acid; sodium acetate / 25 - 30 °C 2.2: 10 - 65 °C 3.1: N-ethyl-N,N-diisopropylamine / acetone / Reflux 4.1: potassium carbonate; tetrabutylammomium bromide / dimethyl sulfoxide / 20 - 80 °C View Scheme

: 90801-87-9
4-(N-methylamino)-1H-imidazole-5-carboxamide

: 853029-57-9
2-bromo-1-(but-2-ynyl)-4-methyl-6-((4-methylquinazolin-2-yl)methyl)-1H-imidazo[4,5-b]pyridine-5,7-(4H,6H)-dione

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: perchloric acid adsorbed on silica gel; formic acid / ethanol / 0.33 h / 20 °C 2: sodium acetate; acetic acid; bromine / 3 h / 65 °C 3: triethylamine / N,N-dimethyl-formamide / 10 h / 20 °C 4: potassium carbonate / N,N-dimethyl-formamide / 8 h / 90 °C View Scheme

: 3-(R)-aminopiperidine dihydrochloride

: 853029-57-9
2-bromo-1-(but-2-ynyl)-4-methyl-6-((4-methylquinazolin-2-yl)methyl)-1H-imidazo[4,5-b]pyridine-5,7-(4H,6H)-dione

: Linagliptin

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 60 - 70℃; for 7h; Large scale;	96.7%
With triethyl borane; sodium carbonate; 4-methyl-2-pentanone at 95 - 100℃; for 10h; Concentration;	93.8%
With potassium carbonate; potassium iodide In acetic acid butyl ester; toluene at 40 - 125℃; pH=11 - 12; Solvent;	47%

: 853029-57-9
2-bromo-1-(but-2-ynyl)-4-methyl-6-((4-methylquinazolin-2-yl)methyl)-1H-imidazo[4,5-b]pyridine-5,7-(4H,6H)-dione

: C13H26N2*C4H6O6

: C31H42N8O2Si2

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In 1-methyl-pyrrolidin-2-one at 80℃;	96%

: 309956-78-3
(R)-piperidin-3-ylcarbamic acid tert-butyl ester

: 853029-57-9
2-bromo-1-(but-2-ynyl)-4-methyl-6-((4-methylquinazolin-2-yl)methyl)-1H-imidazo[4,5-b]pyridine-5,7-(4H,6H)-dione

: 1-[(4-methyl-quinazolin-2-yl)methyl]-3-methyl-7-(2-butyn-1-yl)-8-[(R)-3-(tert-butoxycarbonylamino)-piperidin-1-yl]-2,6-dioxo-2,3,6,7-tetrahydro-1H-purine

Conditions

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide; acetonitrile at 84 - 86℃; for 20h;	95.3%
With potassium carbonate In dimethyl sulfoxide; acetonitrile at 20 - 86℃; for 20h; Temperature;	95.3%
With potassium carbonate; potassium iodide In dimethyl sulfoxide at 80 - 85℃; Reagent/catalyst;	91%

: 853029-57-9
2-bromo-1-(but-2-ynyl)-4-methyl-6-((4-methylquinazolin-2-yl)methyl)-1H-imidazo[4,5-b]pyridine-5,7-(4H,6H)-dione

: C20H20N2O2*C4H6O6

: C40H36N8O4

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In 1-methyl-pyrrolidin-2-one at 140℃; for 3h;	95%

: 853029-57-9
2-bromo-1-(but-2-ynyl)-4-methyl-6-((4-methylquinazolin-2-yl)methyl)-1H-imidazo[4,5-b]pyridine-5,7-(4H,6H)-dione

: C7H10N2O2S2*C4H6O6

: C27H26N8O4S2

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In 1-methyl-pyrrolidin-2-one at 80℃; for 3h;	94.3%

: 853029-57-9
2-bromo-1-(but-2-ynyl)-4-methyl-6-((4-methylquinazolin-2-yl)methyl)-1H-imidazo[4,5-b]pyridine-5,7-(4H,6H)-dione

: 141-43-5
ethanolamine

: 7-(but-2-yn-1-yl)-8-((2-hydroxyethyl)amino)-3-methyl-1-((4-methylquinazolin-2-yl)methyl)-1H-purine-2,6(3H,7H)-dione

Conditions

Conditions	Yield
In toluene for 2h; Reflux;	94.2%

: 853029-57-9
2-bromo-1-(but-2-ynyl)-4-methyl-6-((4-methylquinazolin-2-yl)methyl)-1H-imidazo[4,5-b]pyridine-5,7-(4H,6H)-dione

: C13H10Cl4N2O2*C4H6O6

: C33H26Cl4N8O4

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In 1-methyl-pyrrolidin-2-one at 80 - 140℃; for 3h;	94.1%

: 853029-57-9
2-bromo-1-(but-2-ynyl)-4-methyl-6-((4-methylquinazolin-2-yl)methyl)-1H-imidazo[4,5-b]pyridine-5,7-(4H,6H)-dione

: 886588-62-1
(R)-2-(piperidin-3-yl)isoindoline-1,3-dione D-(-)-tartaric acid salt

: 886588-63-2
(R)-7-(but-2-yn-1-yl)-8-(3-(1,3-dioxoisoindolin-2-yl)piperidin-1-yl)-3-methyl-1-((4-methylquinazolin-2-yl)methyl)-3,7-dihydro-1H-purine2,6-dione

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In 1-methyl-pyrrolidin-2-one at 140℃; for 2h;	94%

: 853029-57-9
2-bromo-1-(but-2-ynyl)-4-methyl-6-((4-methylquinazolin-2-yl)methyl)-1H-imidazo[4,5-b]pyridine-5,7-(4H,6H)-dione

: C21H20N2O2*C4H6O6

: C41H36N8O4

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In 1-methyl-pyrrolidin-2-one at 140℃;	92%

: 853029-57-9
2-bromo-1-(but-2-ynyl)-4-methyl-6-((4-methylquinazolin-2-yl)methyl)-1H-imidazo[4,5-b]pyridine-5,7-(4H,6H)-dione

: C11H18N2*C4H6O6

: C31H34N8O2

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In 1-methyl-pyrrolidin-2-one at 100℃;	92%

: 853029-57-9
2-bromo-1-(but-2-ynyl)-4-methyl-6-((4-methylquinazolin-2-yl)methyl)-1H-imidazo[4,5-b]pyridine-5,7-(4H,6H)-dione

: (R)-3-(benzylideneamino)piperidine

: (R)-8-(3-(benzylideneamino)piperidin-1-yl)-7-(but-2-yn-1-yl)-3-methyl-1-((4-methylquinazolin-2-yl)methyl)-3,7-dihydro-1H-purine-2,6-dione

Conditions

Conditions	Yield
With potassium carbonate In toluene at 100℃; Temperature;	91.2%

: 666816-98-4
8-bromo-7-(but-2-yn-1-yl)-3-methyl-2,,6-dihydro-1H-purine-2,6-dione

: 853029-57-9
2-bromo-1-(but-2-ynyl)-4-methyl-6-((4-methylquinazolin-2-yl)methyl)-1H-imidazo[4,5-b]pyridine-5,7-(4H,6H)-dione

: 886588-63-2
(R)-7-(but-2-yn-1-yl)-8-(3-(1,3-dioxoisoindolin-2-yl)piperidin-1-yl)-3-methyl-1-((4-methylquinazolin-2-yl)methyl)-3,7-dihydro-1H-purine2,6-dione

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In 1-methyl-pyrrolidin-2-one at 140℃; for 2h;	90%

: 853029-57-9
2-bromo-1-(but-2-ynyl)-4-methyl-6-((4-methylquinazolin-2-yl)methyl)-1H-imidazo[4,5-b]pyridine-5,7-(4H,6H)-dione

: (R)-3-piperidinyl phthalimide hydrochloride

: 886588-63-2
(R)-7-(but-2-yn-1-yl)-8-(3-(1,3-dioxoisoindolin-2-yl)piperidin-1-yl)-3-methyl-1-((4-methylquinazolin-2-yl)methyl)-3,7-dihydro-1H-purine2,6-dione

Conditions

Conditions	Yield
Stage #1: 2-bromo-1-(but-2-ynyl)-4-methyl-6-((4-methylquinazolin-2-yl)methyl)-1H-imidazo[4,5-b]pyridine-5,7-(4H,6H)-dione; 3-(R)-piperidinyl phthalimide hydrochloride With potassium carbonate In Isopropyl acetate for 0.5h; Stage #2: With benzyltrimethylammonium chloride In Isopropyl acetate for 16h; Solvent; Reflux;	88.7%

: 853029-57-9
2-bromo-1-(but-2-ynyl)-4-methyl-6-((4-methylquinazolin-2-yl)methyl)-1H-imidazo[4,5-b]pyridine-5,7-(4H,6H)-dione

: 124-40-3
dimethyl amine

: 7-(but-2-yn-1-yl)-8-(dimethylamino)-3-methyl-1-[(4-methylquinazolin-2-yl)methyl]-3,7-dihydro-1H-purine-2,6-dione

Conditions

Conditions	Yield
With sodium carbonate In N,N-dimethyl-formamide at 25 - 55℃; for 24h; Inert atmosphere;	71.66%

: 853029-57-9
2-bromo-1-(but-2-ynyl)-4-methyl-6-((4-methylquinazolin-2-yl)methyl)-1H-imidazo[4,5-b]pyridine-5,7-(4H,6H)-dione

: 103831-11-4, 116183-81-4, 116183-83-6, 122458-34-8
(3R)-3-aminopyrrolidine dihydrochloride

: (R)-8-(3-aminopyrrolidin-1-yl)-7-(but-2-ynyl)-3-methyl-1-[(4-methylquinazolin-2-yl)methyl]-1H-purine-2,6(3H,7H)-dione

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 75℃; for 6h;	70%

: 110-89-4
piperidine

: 853029-57-9
2-bromo-1-(but-2-ynyl)-4-methyl-6-((4-methylquinazolin-2-yl)methyl)-1H-imidazo[4,5-b]pyridine-5,7-(4H,6H)-dione

: 7-(but-2-ynyl)-3-methyl-1-((4-methylquinazolin-2-yl)methyl)-8-(piperidin-1-yl)-1H-purine-2,6(3H,7H)-dione

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 6h;	67%

: 110-85-0
piperazine

: 853029-57-9
2-bromo-1-(but-2-ynyl)-4-methyl-6-((4-methylquinazolin-2-yl)methyl)-1H-imidazo[4,5-b]pyridine-5,7-(4H,6H)-dione

: 7-(but-2-yn-1-yl)-3-methyl-1-((4-methylquinazolin-2-yl)methyl)-8-(piperazin-1-yl)-1H-purine-2,6(3H,7H)-dione

Conditions

Conditions	Yield
In DMF (N,N-dimethyl-formamide) at 200℃; for 0.0833333h; Microwave irradiation;	66%
With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 6h;	58%

: 853029-57-9
2-bromo-1-(but-2-ynyl)-4-methyl-6-((4-methylquinazolin-2-yl)methyl)-1H-imidazo[4,5-b]pyridine-5,7-(4H,6H)-dione

: 103831-11-4, 116183-81-4, 116183-83-6, 122458-34-8
(S)-3-aminopyrrolidine dihydrochloride

: (S)-8-(3-aminopyrrolidin-1-yl)-7-(but-2-ynyl)-3-methyl-1-[(4-methylquinazolin-2-yl)methyl]-1H-purine-2,6(3H,7H)-dione

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 75℃; for 6h;	65%

: 853029-57-9
2-bromo-1-(but-2-ynyl)-4-methyl-6-((4-methylquinazolin-2-yl)methyl)-1H-imidazo[4,5-b]pyridine-5,7-(4H,6H)-dione

: 216854-23-8
tert-butyl (S)-piperidin-3-yl-carbamate

: 668273-74-3
1-[(4-methyl-quinazolin-2-yl)methyl]-3-methyl-7-(2-butyn-1-yl)-8-(3-(S)-tert-butoxycarbonylaminopiperidin-1-yl)xanthine

Conditions

Conditions	Yield
With potassium carbonate In tetrahydrofuran for 16h; Reflux;	65%

: 853029-57-9
2-bromo-1-(but-2-ynyl)-4-methyl-6-((4-methylquinazolin-2-yl)methyl)-1H-imidazo[4,5-b]pyridine-5,7-(4H,6H)-dione

: (R)-1-cyclohexyl-N-(piperidin-3-yl)methanimine

: (R)-7-(but-2-yn-1-yl)-8-(3-((cyclohexylmethylen)amino)piperidin-1-yl)-3-methyl-1-((4-methyilquinazolin-2-yl)methyl)-3,7-dihydro-1H-purin-2,6-dione

Conditions

Conditions	Yield
With potassium phosphate In 1-methyl-pyrrolidin-2-one; toluene at 103℃;	64.2%

: 853029-57-9
2-bromo-1-(but-2-ynyl)-4-methyl-6-((4-methylquinazolin-2-yl)methyl)-1H-imidazo[4,5-b]pyridine-5,7-(4H,6H)-dione

: 93643-24-4
(S)-octahydropyrrolo[1,2-a]pyrazine

: (S)-7-(but-2-ynyl)-8-(hexahydropyrrolo[1,2-a]pyrazin-2(1H)-yl)-3-methyl-1-((4-methylquinazolin-2-yl)methyl)-1H-purine-2,6(3H,7H)-dione

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 75℃; for 6h;	60%

: 853029-57-9
2-bromo-1-(but-2-ynyl)-4-methyl-6-((4-methylquinazolin-2-yl)methyl)-1H-imidazo[4,5-b]pyridine-5,7-(4H,6H)-dione

: 3-phenyl-N-((R)-piperidin-3-yl)prop-2-en-1-imine

: 7-(but-2-yn-1-yl)-3-methyl-1-((4-methylquinazolin-2-yl)methyl)-8-((R)-3-(((1E,2E)-3-phenylallylidene)amino)piperidin-1-yl)-3,7-dihydro-1H-purine-2,6-dione

Conditions

Conditions	Yield
With potassium phosphate In 1-methyl-pyrrolidin-2-one; toluene at 103℃;	56.5%

: 853029-57-9
2-bromo-1-(but-2-ynyl)-4-methyl-6-((4-methylquinazolin-2-yl)methyl)-1H-imidazo[4,5-b]pyridine-5,7-(4H,6H)-dione

: (R)-1-(4-methylphenyl)-N-(piperidin-3-yl)methanimine

: (R)-8-(3-(4-methylbenzylideneamino)piperidin-1-yl)-7-(but-2-yn-1-yl)-3-methyl-1-((4-methylquinazolin-2-yl)methyl)-3,7-dihydro-1H-purine-2,6-dione

Conditions

Conditions	Yield
With potassium phosphate In 1-methyl-pyrrolidin-2-one; toluene at 103℃;	54.7%

: 853029-57-9
2-bromo-1-(but-2-ynyl)-4-methyl-6-((4-methylquinazolin-2-yl)methyl)-1H-imidazo[4,5-b]pyridine-5,7-(4H,6H)-dione

: (R)-1-(4-nitrophenyl)-N-(piperidin-3-yl)methanimine

: (R)-8-(3-(4-nitrobenzylideneamino)piperidin-1-yl)-7-(but-2-yn-1-yl)-3-methyl-1-((4-methylquinazolin-2-yl)methyl)-3,7-dihydro-1H-purine-2,6-dione

Conditions

Conditions	Yield
With potassium phosphate In 1-methyl-pyrrolidin-2-one; toluene at 103℃;	54.7%

8-Bromo-7-(2-butyn-1-yl)-3,7-dihydro-3-methyl-1-[(4-methyl-2-quinazolinyl)methyl]-1H-purine-2,6-dione Specification

The 1H-Purine-2,6-dione,8-bromo-7-(2-butynyl)-3,7-dihydro-3-methyl-1-[(4-methyl-2-quinazolinyl)methyl]-, with the CAS registry number 853029-57-9, is also known as 1-[(4-Methylquinazolin-2-yl)methyl]-3-methyl-7-(2-butyn-1-yl)-8-bromoxanthine. This chemical's molecular formula is C₂₀H₁₇BrN₆O₂ and molecular weight is 453.00. What's more, its systematic name is called 8-Bromo-7-(2-butyn-1-yl)-3-methyl-1-[(4-methyl-2-quinazolinyl)methyl]-3,7-dihydro-1H-purine-2,6-dione.

Physical properties about 1H-Purine-2,6-dione,8-bromo-7-(2-butynyl)-3,7-dihydro-3-methyl-1-[(4-methyl-2-quinazolinyl)methyl]- are: (1)ACD/LogP: 3.96±1.01; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.96 ; (4)ACD/LogD (pH 7.4): 3.96; (5)ACD/BCF (pH 5.5): 598.76; (6)ACD/BCF (pH 7.4): 599.37; (7)ACD/KOC (pH 5.5): 3384.03; (8)ACD/KOC (pH 7.4): 3387.48; (9)#H bond acceptors: 8; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 3; (12)Polar Surface Area: 84.22 Å²; (13)Index of Refraction: 1.713; (14)Molar Refractivity: 114.3±0.5 cm³; (15)Molar Volume: 291.3±7.0 cm³; (16)Polarizability: 45.3±0.5×10^-24cm³; (17)Surface Tension: 57.2±7.0 dyne/cm; (18)Density: 1.6±0.1 g/cm³; (19)Flash Point: 291.8±32.9 °C; (20)Enthalpy of Vaporization: 84.1±3.0 kJ/mol; (21)Boiling Point: 558.8±60.0 °C at 760 mmHg; (22)Vapour Pressure: 0.0±1.5 mmHg at 25 °C.

You can still convert the following datas into molecular structure:
(1) SMILES: CC#CCn1c2c(nc1Br)n(c(=O)n(c2=O)Cc3nc(c4ccccc4n3)C)C
(2) InChI: InChI=1S/C20H17BrN6O2/c1-4-5-10-26-16-17(24-19(26)21)25(3)20(29)27(18(16)28)11-15-22-12(2)13-8-6-7-9-14(13)23-15/h6-9H,10-11H2,1-3H3
(3) InChIKey: RCZJXCXNYGHNSR-UHFFFAOYSA-N

Product Name

8-Bromo-7-but-2-ynyl-3-methyl-1-(4-methyl-quinazolin-2-ylmethyl)-3,7-dihydro-purine-2,6-dione

Synthetic route

8-Bromo-7-(2-butyn-1-yl)-3,7-dihydro-3-methyl-1-[(4-methyl-2-quinazolinyl)methyl]-1H-purine-2,6-dione Specification

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