2-(Chloromethyl)-4-methylquinazoline supplier

Name
2-(chloromethyl)-4-methylquinazoline
EINECS 1308068-626-2
CAS No. 109113-72-6
Article Data9
CAS DataBase
Density 1.251 g/cm³
Solubility 3.11g/L at 20℃
Melting Point 61 - 63 °C
Formula C₁₀H₉ClN₂
Boiling Point 240.039 °C at 760 mmHg
Molecular Weight 192.648
Flash Point 122.14 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms MFCD09807547;NSC 48971;2-Amino-3,4-dimethylbenzoic acid;2-(Chloromethyl)-4-methylquinazoline;
PSA 25.78000
LogP 2.67700

Synthetic route

: 551-93-9
2-aminoacetophenone

: 79-07-2
Chloroacetamide

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

Conditions

Conditions	Yield
Stage #1: 2-aminoacetophenone With phosphoric acid In ethanol at 20℃; Stage #2: Chloroacetamide In ethanol Reagent/catalyst; Solvent; Reflux;	94.26%
With oxygen; triethylamine; copper(l) chloride In tetrahydrofuran for 12h; Reflux;	88%

: 551-93-9
2-aminoacetophenone

: 107-14-2
chloroacetonitrile

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

Conditions

Conditions	Yield
With hydrogenchloride In 1,4-dioxane at 6℃; for 2h;	85%
With hydrogenchloride; [1-(3-sulfonic acid)]propyl-3-methylimidazolium hydrogen sulfate In 1,4-dioxane; water at 8℃; for 18h; Reagent/catalyst; Temperature;	85.14%
Stage #1: 2-aminoacetophenone With hydrogenchloride In 1,4-dioxane at 10℃; Cooling; Stage #2: chloroacetonitrile In 1,4-dioxane at -10℃; for 1h;	45%

: 107-14-2
chloroacetonitrile

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

Conditions

Conditions	Yield
Stage #1: 2-aminoacetophenone With hydrogenchloride In 1,4-dioxane at -10 - 25℃; Stage #2: chloroacetonitrile In 1,4-dioxane at -10 - 2℃; for 3h; Stage #3: With sodium hydroxide In 1,4-dioxane; water at 5 - 11℃;	74%

: 6640-59-1
2-(chloromethyl)-4-methylquinazoline 3-oxide

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

Conditions

Conditions	Yield
With phosphorus trichloride In chloroform Heating / reflux;	57%

: 70656-87-0
Ro 5-3663

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

Conditions

Conditions	Yield
With trichlorophosphate for 0.5h; Heating;	52%

: 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%

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

: 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

: 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
Stage #1: 8-bromo-7-(but-2-yn-1-yl)-3-methyl-3,7-dihydro-1H-purine-2,6-dione; 2-chloromethyl-4-methylquinazoline With potassium carbonate In 1-methyl-pyrrolidin-2-one; acetonitrile at 50℃; for 6h; Stage #2: (R)-piperidin-3-ylcarbamic acid tert-butyl ester In 1-methyl-pyrrolidin-2-one; acetonitrile at 60℃; for 8h; Solvent; Temperature;	95.1%
With sodium carbonate at 55 - 60℃; for 6h; Concentration; Reagent/catalyst;	91.8%
Stage #1: (R)-piperidin-3-ylcarbamic acid tert-butyl ester; 8-bromo-7-(but-2-yn-1-yl)-3-methyl-3,7-dihydro-1H-purine-2,6-dione With 1-methyl-pyrrolidin-2-one; potassium carbonate; potassium iodide for 10h; Stage #2: 2-chloromethyl-4-methylquinazoline for 12h; Time;	90%
Stage #1: 8-bromo-7-(but-2-yn-1-yl)-3-methyl-3,7-dihydro-1H-purine-2,6-dione; 2-chloromethyl-4-methylquinazoline With potassium carbonate; potassium iodide In 1-methyl-pyrrolidin-2-one at 40 - 50℃; Stage #2: (R)-piperidin-3-ylcarbamic acid tert-butyl ester Reagent/catalyst; Solvent; Temperature;	86.7%
Stage #1: 8-bromo-7-(but-2-yn-1-yl)-3-methyl-3,7-dihydro-1H-purine-2,6-dione; 2-chloromethyl-4-methylquinazoline With potassium carbonate; potassium iodide In 1-methyl-pyrrolidin-2-one at 40 - 50℃; Stage #2: (R)-piperidin-3-ylcarbamic acid tert-butyl ester In 1-methyl-pyrrolidin-2-one Reagent/catalyst; Solvent; Temperature;

...Expand

: 8-[(R)-3-aminopiperidin-1-yl]-3,7-dihydro-3-methyl-7-(2-butynyl)-1H-purine-2,6-dione

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

: Linagliptin

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 10h;	94.8%
With sodium hydrogencarbonate In 1-methyl-pyrrolidin-2-one at 90℃; Solvent; Temperature;	1.8 g

: 705280-62-2
2-bromo-3-(2-butyn-1-yl)-3,5-dihydro-imidazo[4,5-d]pyridazin-4-one

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

: 705280-63-3
2-bromo-3-(2-butyn-1-yl)-5-[(4-methyl-quinazolin-2-yl)methyl]-3,5-dihydro-imidazo[4,5-d]pyridazin-4-one

Conditions

Conditions	Yield
With caesium carbonate In DMF (N,N-dimethyl-formamide) at 80℃; for 1h;	94%
With caesium carbonate In DMF (N,N-dimethyl-formamide) at 80℃; for 1h;	94%
With potassium carbonate In 1-methyl-pyrrolidin-2-one at 80℃; for 3h;	75%

: 615-77-0
1-methyluracil

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

: C15H14N4O2

Conditions

Conditions	Yield
With triethylamine In 1-methyl-pyrrolidin-2-one at 80 - 85℃; Reagent/catalyst; Solvent; Temperature;	93.6%
With triethylamine In 1-methyl-pyrrolidin-2-one at 80 - 85℃; for 34h; Solvent; Temperature; Reagent/catalyst;	93.6%

: 8-iodine-7-(2-butynyl)-3-methyl-1H-purine-2,6(3H,7H)-dione

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

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

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 8h;	93.2%
Stage #1: 8-iodine-7-(2-butynyl)-3-methyl-1H-purine-2,6(3H,7H)-dione; 2-chloromethyl-4-methylquinazoline With sodium carbonate In 1-methyl-pyrrolidin-2-one at 90℃; for 11h; Stage #2: With acetic acid In ethanol at 60℃; for 0.5h;	65%

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

: 886588-61-0
C13H14N2O2

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

: 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: 8-bromo-7-(but-2-yn-1-yl)-3-methyl-3,7-dihydro-1H-purine-2,6-dione; C13H14N2O2 With 1-methyl-pyrrolidin-2-one; potassium carbonate; potassium iodide at 50 - 60℃; Stage #2: 2-chloromethyl-4-methylquinazoline	91%

...Expand

: 1431528-74-3
1-(but-2-yn-1-yl)-6-chloropyrimidine-2,4(1H,3H)-dione

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

: 1-(2-butyn-1-yl)-6-chloro-3-[(4-methylquinazolin-2-yl)methyl]pyrimidine-2,4 (1H,3H)-dione

Conditions

Conditions	Yield
Stage #1: 1-(but-2-yn-1-yl)-6-chloropyrimidine-2,4(1H,3H)-dione With sodium hydride; lithium bromide In N,N-dimethyl-formamide at 0℃; for 0.5h; Inert atmosphere; Stage #2: 2-chloromethyl-4-methylquinazoline In N,N-dimethyl-formamide at 80℃; Inert atmosphere;	88%
Stage #1: 1-(but-2-yn-1-yl)-6-chloropyrimidine-2,4(1H,3H)-dione With sodium hydride In dimethyl sulfoxide; N,N-dimethyl-formamide at 0℃; for 0.0833333h; Stage #2: With lithium bromide In dimethyl sulfoxide; N,N-dimethyl-formamide for 0.25h; Stage #3: 2-chloromethyl-4-methylquinazoline In dimethyl sulfoxide; N,N-dimethyl-formamide at 20℃;	86.5%

: 1431528-74-3
1-(but-2-yn-1-yl)-6-chloropyrimidine-2,4(1H,3H)-dione

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

: 1-methyl-6-chloro-3-[(4-methylquinazolin-2-yl)methyl]pyrimidine-2,4(1H,3H)-dione

Conditions

Conditions	Yield
Stage #1: 1-(but-2-yn-1-yl)-6-chloropyrimidine-2,4(1H,3H)-dione With sodium hydride In dimethyl sulfoxide; N,N-dimethyl-formamide at 0℃; for 0.0833333h; Stage #2: With lithium bromide In dimethyl sulfoxide; N,N-dimethyl-formamide for 0.25h; Stage #3: 2-chloromethyl-4-methylquinazoline In dimethyl sulfoxide; N,N-dimethyl-formamide at 20℃;	86.5%

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

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

: C19H17BrN6O2S

Conditions

Conditions	Yield
Stage #1: 8-bromo-3-methyl-7-(thietan-3-yl)-3,7-dihydro-1H-pyrine-2,6-dione With potassium hydroxide In water; N,N-dimethyl-formamide for 0.5h; Stage #2: 2-chloromethyl-4-methylquinazoline In water; N,N-dimethyl-formamide at 20℃; for 6h;	86%

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

: 25137-01-3
(R)-ethyl nipecotate

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

: C28H31N7O4

Conditions

Conditions	Yield
Stage #1: 8-bromo-7-(but-2-yn-1-yl)-3-methyl-3,7-dihydro-1H-purine-2,6-dione; (R)-ethyl nipecotate With 1-methyl-pyrrolidin-2-one; potassium carbonate; potassium iodide at 60 - 70℃; Stage #2: 2-chloromethyl-4-methylquinazoline	85%

...Expand

: 666816-91-7
3-methyl-7-(2-butyn-1-yl)-8-[(R)-3-(tert-butoxycarbonylamino)piperidin-1-yl]xanthine

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

: 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 tetrabutylammomium bromide; potassium carbonate In cyclohexane Reagent/catalyst; Solvent; Reflux;	80.3%

: 8-bromo-3-methyl-7-(prop-2-ynyl)-1H-purine-2,6(3H,7H)-dione

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

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

Conditions

Conditions	Yield
With sodium carbonate In N,N-dimethyl-formamide at 80℃; for 12h;	80%

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

: 1-(3-methyl-2-buten-1-yl)-6-chloro-3-[(4-methylquinazolin-2-yl)methyl]pyrimidine-2,4(1H,3H)-dione

: 75-07-0
acetaldehyde

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

: 4,4'-(2-methylpropane-1,3-diyl)bis(2-chloromethylquinazoline)

Conditions

Conditions	Yield
With sodium hydroxide In 1,4-dioxane; water at 10 - 25℃; for 17.5h;	77.78%

: 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

: C20H17BrN6O2

Conditions

Conditions	Yield
Stage #1: 8-bromo-7-(but-2-yn-1-yl)-3-methyl-2,,6-dihydro-1H-purine-2,6-dione With chloro-trimethyl-silane; trimethylsilyl trifluoromethanesulfonate In toluene for 24h; Reflux; Stage #2: 2-chloromethyl-4-methylquinazoline With sodium hydride In N,N-dimethyl-formamide at 0 - 10℃; for 5h;	72.5%

: 7-allyl-8-bromo-3-methyl-1H-purine-2,6(3H,7H)-dione

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

: 7-allyl-8-bromo-3-methyl-1-[(4-methylquinazolin-2-yl)methyl]-1H-purine-2,6(3H,7H)-dione

Conditions

Conditions	Yield
With sodium carbonate In N,N-dimethyl-formamide at 80℃; for 12h;	72%

: C23H22N6O4

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

: 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 potassium carbonate In tetrahydrofuran for 25h; Reflux;	69.8%

: 1-allyl-6-chloropyrimidine-2,4(1H,3H)-dione

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

: 1-allyl-6-chloro-3-[(4-methylquinazolin-2-yl)methyl]pyrimidine-2,4(1H,3H)-dione

Conditions

Conditions	Yield
Stage #1: 1-allyl-6-chloropyrimidine-2,4(1H,3H)-dione With sodium hydride; lithium bromide In N,N-dimethyl-formamide at 0℃; for 0.5h; Inert atmosphere; Stage #2: 2-chloromethyl-4-methylquinazoline In N,N-dimethyl-formamide at 80℃; Inert atmosphere;	65%

: 3-(R)-aminopiperidine dihydrochloride

: 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

: Linagliptin

Conditions

Conditions	Yield
Stage #1: 8-bromo-7-(but-2-yn-1-yl)-3-methyl-3,7-dihydro-1H-purine-2,6-dione; 2-chloromethyl-4-methylquinazoline With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 6h; Stage #2: 3-(R)-aminopiperidine dihydrochloride With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 8h;	57%
Stage #1: 8-bromo-7-(but-2-yn-1-yl)-3-methyl-3,7-dihydro-1H-purine-2,6-dione; 2-chloromethyl-4-methylquinazoline With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 6h; Stage #2: 3-(R)-aminopiperidine dihydrochloride With potassium carbonate In N,N-dimethyl-formamide at 20 - 80℃; for 8h; Stage #3: pH=8;	57%

...Expand

: 354-38-1
2,2,2-trifluoroacetamide

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

: 2,2,2-trifluoro-N-((4-methylquinazolin-2-yl)methyl)acetamide

Conditions

Conditions	Yield
Stage #1: 2,2,2-trifluoroacetamide With caesium carbonate In tetrahydrofuran at 20℃; for 0.0833333h; Inert atmosphere; Stage #2: 2-chloromethyl-4-methylquinazoline In tetrahydrofuran at 65℃; for 16h; Inert atmosphere;	55%

: 865758-95-8
2-[(6-chloro-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)methyl]benzonitrile

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

: 6-chloro-1-(2-cyanobenzyl)-3-[(4-methylquinazolin-2-yl)methyl]pyrimidine-2,4(1H,3H)-dione

Conditions

Conditions	Yield
Stage #1: 2-[(6-chloro-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)methyl]benzonitrile With sodium hydride; lithium bromide In N,N-dimethyl-formamide at 0℃; for 0.5h; Inert atmosphere; Stage #2: 2-chloromethyl-4-methylquinazoline In N,N-dimethyl-formamide at 80℃; Inert atmosphere;	50%

: 107099-99-0
2,5-dimethoxyphenylboronic acid

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

: 1416422-98-4
C18H18N2O2

Conditions

Conditions	Yield
With potassium phosphate; C12H10ClNPd*C16H21O3P In tetrahydrofuran; water at 60℃; for 20h;	24%

: 6-chloro-1-(prop-2-ynyl)pyrimidine-2,4(1H,3H)-dione

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

: 6-chloro-3-[(4-methylquinazolin-2-yl)methyl]-1-(prop-2-ynyl)pyrimidine-2,4(1H,3H)-dione

Conditions

Conditions	Yield
Stage #1: 6-chloro-1-(prop-2-ynyl)pyrimidine-2,4(1H,3H)-dione With sodium hydride; lithium bromide In N,N-dimethyl-formamide at 0℃; for 0.5h; Inert atmosphere; Stage #2: 2-chloromethyl-4-methylquinazoline In N,N-dimethyl-formamide at 80℃; Inert atmosphere;	22%

2-(Chloromethyl)-4-methylquinazoline Specification

The 2-(Chloromethyl)-4-methylquinazoline, with the CAS registry number 109113-72-6, is also known as 2-Amino-3,4-dimethylbenzoic acid. This chemical's molecular formula is C₁₀H₉ClN₂ and molecular weight is 192.64. What's more, its systematic name is 2-(Chloromethyl)-4-methylquinazoline.

Physical properties of 2-(Chloromethyl)-4-methylquinazoline are: (1)ACD/LogP: 2.009; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.01; (4)ACD/LogD (pH 7.4): 2.01; (5)ACD/BCF (pH 5.5): 19.78; (6)ACD/BCF (pH 7.4): 19.79; (7)ACD/KOC (pH 5.5): 294.75; (8)ACD/KOC (pH 7.4): 294.87; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 25.78 Å²; (13)Index of Refraction: 1.631; (14)Molar Refractivity: 54.868 cm³; (15)Molar Volume: 153.967 cm³; (16)Polarizability: 21.752×10^-24cm³; (17)Surface Tension: 51.42 dyne/cm; (18)Density: 1.251 g/cm³; (19)Flash Point: 122.14 °C; (20)Enthalpy of Vaporization: 45.761 kJ/mol; (21)Boiling Point: 240.039 °C at 760 mmHg; (22)Vapour Pressure: 0.06 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: ClCc2nc1c(cccc1)c(n2)
(2)Std. InChI: InChI=1S/C10H9ClN2/c1-7-8-4-2-3-5-9(8)13-10(6-11)12-7/h2-5H,6H2,1H3
(3)Std. InChIKey: UHCUBOJGMLASBY-UHFFFAOYSA-N

Product Name

2-(chloromethyl)-4-methylquinazoline

Synthetic route

2-(Chloromethyl)-4-methylquinazoline Specification

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