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Quality Control of [ 591227-12-2 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 591227-12-2 ]

Product Details of [ 591227-12-2 ]

CAS No. :	591227-12-2	MDL No. :	MFCD21607288
Formula :	C₁₂H₁₀N₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	210.24	Pubchem ID :	-
Synonyms :

Safety of [ 591227-12-2 ]

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Application In Synthesis of [ 591227-12-2 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 591227-12-2 ]

[ 591227-12-2 ] Synthesis Path-Downstream 1~8

1
[ 156-81-0 ]
[ 70-11-1 ]
[ 591227-12-2 ]

Yield	Reaction Conditions	Operation in experiment
		Step 1: 2-Phenyl-imidazo[1,2-a]pyrimidin-7-ylamine Bromoacetophenone (2.71 g, 14 mmol) was added to a solution of <strong>[156-81-0]2,4-diaminopyrimidine</strong> (1.00 g, 9 mmol) in acetone (40 ml), and the mixture was heated to reflux for 5 h. The cooled suspension was filtered, the precipitate was washed (acetone), and then stirred for 15 min in a mixture of 10 ml water and 15 ml NH4OH (25%). The suspension was filtered, washed (water), and dried under vacuum. The crude product (1.9 g, quant.) was used in the next step without further purification. MS (m/e)=211.1 [M+H+].
		Bromoacetophenone (2.71 g, 14 mrnol) was added to a solution of <strong>[156-81-0]2,4-diaminopyrimidine</strong> (1.00 g, 9 mrnol) in acetone (40 ml), and the mixture was heated to reflux for 5 h. The cooled suspension was filtered, the precipitate was washed (acetone), and then stirred for 15 min in a mixture of 10 ml water and 15 ml NH4OH (25%). The suspension was filtered, washed (water), and dried under vacuum. The crude product (1.9 g, quant.) was used in the next step without further purification.MS (m/e) = 211.1 [M+H+].

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 7350 - 7370
[2]Patent: US2011/237564,2011,A1 .Location in patent: Page/Page column 19
[3]Patent: WO2011/117264,2011,A1 .Location in patent: Page/Page column 56

2
[ 4744-50-7 ]
[ 591227-12-2 ]
[ 1335299-50-7 ]

Yield	Reaction Conditions	Operation in experiment
	dmap; In N,N-dimethyl-formamide; at 78℃;	Step 1: 3-(2-Phenyl-imidazo[1,2-a]pyrimidin-7-ylcarbamoyl)-pyrazine-2-carboxylic acid Furo[3,4-b]pyrazine-5,7-dione (736 mg, 4.9 mmol) and DMAP (58 mg, cat.) were added to a solution of 2-phenyl-imidazo[1,2-a]pyrimidin-7-ylamine (example 1, step 1, 1.00 g, 4.8 mmol) in DMF (25 ml). The mixture was heated to 78 C. overnight, and cooled to RT. The formed precipitate was collected by filtration, and residual solvent was removed under vacuum. The thus obtained crude product (800 mg, 47%) was used in the next step without further purification. MS (m/e)=361.3 [M+H+].
	With dmap; In N,N-dimethyl-formamide; at 78℃;	Furo[3,4-b]pyrazine-5,7-dione (736 mg, 4.9 mmol) and DMAP (58 mg, cat.) were added to a solution of 2-phenyl- imidazo [l,2-a]pyrimidin-7-ylamine (example 1, step 1, 1.00 g, 4.8 mmol) in DMF (25 ml). The mixture was heated to 78C overnight, and cooled to RT. The formed precipitate was collected by filtration, and residual solvent was removed under vacuum. The thus obtained crude product (800 mg, 47%) was used in the next step without further purification. MS (m/e) = 361.3 [M+H+].

Reference： [1]Patent: US2011/237564,2011,A1 .Location in patent: Page/Page column 28
[2]Patent: WO2011/117264,2011,A1 .Location in patent: Page/Page column 76

3
[ 591227-12-2 ]
[ 16498-81-0 ]
[ 1335299-96-1 ]

Yield	Reaction Conditions	Operation in experiment
11%	With N-ethyl-N,N-diisopropylamine;2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; In tetrahydrofuran; ethyl acetate; at 60℃; for 18h;	Example 78 2-Methoxy-N-(2-phenylimidazo[1,2-a]pyrimidin-7-yl)nicotinamide A mixture of 2-phenylimidazo[1,2-a]pyrimidin-7-amine (200 mg, 951 mumol, Eq: 1.00), <strong>[16498-81-0]2-methoxynicotinic acid</strong> (146 mg, 951 mumol, Eq: 1.00), diisopropylethylamine (369 mg, 498 mul, 2.85 mmol, Eq: 3) and propylphosphonic anhydride in ethyl acetate 50% (1.21 g, 1.12 ml, 1.9 mmol, Eq: 2) in tetrahydrofuran (10 ml) is stirred for 18 hours at 60 C. The mixture is diluted with ethyl acetate and washed 2 times with water and once with brine, the organic layer was separated, dried over magnesium sulfate, filtrated and evaporated. The crude material was applied on silicagel and purified by flash chromatography over a 20 g silicagel column using ethyl acetate/methanol 0-10% as eluent affording 2-methoxy-N-(2-phenylimidazo[1,2-a]pyrimidin-7-yl)nicotinamide (36 mg, 11%) as a light yellow solid. MS: m/e=346.1 (M+H+), mp: 225-226 C.
		A mixture of 2-phenylimidazo[l,2-a]pyrimidin-7-amine (200 mg, 951 muiotaetaomicron, Eq: 1.00), 2- methoxynicotinic acid (146 mg, 951 muetaiotaomicron, Eq: 1.00), diisopropylethylamine (369 mg, 498 mu, 2.85 mmol, Eq: 3) and propylphosphonic anhydride in ethyl acetate 50% (1.21 g, 1.12 ml, 1.9 mmol, Eq: 2) in tetrahydrofuran (10 ml) is stirred for 18 hours at 60 C. The mixture is diluted with ethyl acetate and washed 2 times with water and once with brine, the organic layer was separated, dried over magnesium sulfate, filtrated and evaporated. The crude material was ap lied on silicagel and purified by flash chromatography over a 20 g silicagel column using ethyl acetate / methanol 0-10 % as eluent affording 2-methoxy-N-(2-phenylimidazo[l,2- a]pyrimidin-7-yl)nicotinamide ( 36 mg, 11 %) as a light yellow solid. MS: m/e = 346.1 (M+H+), mp: 225-226 C

Reference： [1]Patent: US2011/237564,2011,A1 .Location in patent: Page/Page column 36
[2]Patent: WO2011/117264,2011,A1 .Location in patent: Page/Page column 96-97

4
[ 25462-85-5 ]
[ 591227-12-2 ]
[ 1335299-99-4 ]

Yield	Reaction Conditions	Operation in experiment
52.9%	With N-ethyl-N,N-diisopropylamine;2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; In tetrahydrofuran; ethyl acetate; for 4h;Reflux;	Example 81 2-Chloro-6-methyl-N-(2-phenylimidazo[1,2-a]pyrimidin-7-yl)isonicotinamide A mixture of 2-phenylimidazo[1,2-a]pyrimidin-7-amine (141 mg, 0.671 mmol, 1 eq.), 2-chroro-6-methylisonicotinic acid (127 mg, 0.738 mmol, 1.1 eq.), propylphosphonic anhydride in ethyl acetate 50% (0.98 ml, 1.68 mmol, 2.5 eq) and ethyldiisopropylamine (0.47 ml, 2.68 mmol, 4 eq) in tetrahydrofurane (10 ml) is refluxed for 4 hours. The mixture is diluted with ethyl acetate and washed with sat. aqueous sodium bicarbonate, twice with water, dried over magnesium sulfate and the solvent is removed in vacuo. Purification of the residue by chromatography on a 20 g Silicycle silica cartridge using ethyl acetate a eluent affords 2-chloro-6-methyl-N-(2-phenyl-imidazo[1,2-a]pyrimidin-7-yl)-isonicotinamide (129 mg, 52.9%) as a yellow solid (cryst. form heptane/ethlyl acetate 7/3). MS: m/e=364.0 (M+H+), mp.: 148-151 C.
		A mixture of 2-phenylimidazo[l,2-a]pyrimidin-7-amine (141 mg, 0.671 mmol, 1 eq.), 2-chroro- 6-methylisonicotinic acid (127 mg, 0.738 mmol, 1.1 eq.), propylphosphonic anhydride in ethyl acetate 50% (0.98 ml, 1.68 mmol, 2.5 eq) and ethyldiisopropylamine (0.47 ml, 2.68 mmol, 4 eq) in tetrahydrofurane (10 ml) is refluxed for 4 hours. The mixture is diluted with ethyl acetate and washed with sat. aqueous sodium bicarbonate, twice with water, dried over magnesium sulfate and the solvent is removed in vacuo. Purification of the residue by chromatography on a 20 g Silicycle silica cartridge using ethyl acetate a eluent affords 2-chloro-6-methyl-N-(2-phenyl- imidazo[l,2-a]pyrimidin-7-yl)-isonicotinamide (129 mg, 52.9%) as a yellow solid (cryst. fom heptane / ethlyl acetate 7/3). MS: m/e = 364.0 (M+H+), mp.: 148-15PC.

Reference： [1]Patent: US2011/237564,2011,A1 .Location in patent: Page/Page column 37
[2]Patent: WO2011/117264,2011,A1 .Location in patent: Page/Page column 98-99

5
[ 213771-32-5 ]
[ 591227-12-2 ]
[ 1335299-16-5 ]

Yield	Reaction Conditions	Operation in experiment
54%		Example 23 5-Bromo-3-methyl-pyridine-2-carboxylic acid (2-phenyl-imidazo[1,2-a]pyrimidin-7-yl)-amide To an argon purged solution of 2-phenylimidazo[1,2-a]pyrimidin-7-amine (example 1, step 1, 80 mg, 0.381 mmol) in dioxane (5 ml) was added trimethyl aluminum solution (0.571 ml, 1.14 mmol, 3 eq). The resulting solution was stirred for 1 hour at RT. Then <strong>[213771-32-5]methyl <strong>[213771-32-5]5-bromo-3-methylpicolinate</strong></strong> (88 mg, 0.381 mmol) was added and the mixture was heated to reflux and stirred for 18 hours. The title compound (84 mg, 54%) was isolated from the crude product by flash chromatography on a 20 g SiO2 column using dichloromethane/methanol 0-10% as eluent. MS (m/e)=408.2 [M+H+].
		To an argon purged solution of 2-phenylimidazo[l,2-a]pyrimidin-7-amine (example 1, step 1, 80 mg, 0.381 mmol) in dioxane (5 ml) was added trimethyl aluminum solution (0.571 ml, 1.14 mmol, 3 eq). The resulting solution was stirred for 1 hour at RT. Then methyl 5-bromo-3- methylpicolinate (88 mg, 0.381 mmol) was added and the mixture was heated to reflux and stirred for 18 hours. The title compound (84 mg, 54%) was isolated from the crude product by flash chromatography on a 20 g Si02 column using dichloromethane / methanol 0-10 % as eluent.MS (m/e) = 408.2 [M+H+].

Reference： [1]Patent: US2011/237564,2011,A1 .Location in patent: Page/Page column 23
[2]Patent: WO2011/117264,2011,A1 .Location in patent: Page/Page column 65-66

6
[ 4021-11-8 ]
[ 591227-12-2 ]
[ 1335299-98-3 ]

Yield	Reaction Conditions	Operation in experiment
17.8%	With N-ethyl-N,N-diisopropylamine;2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; In tetrahydrofuran; ethyl acetate; at 20℃; for 22h;Reflux;	Example 80 2-Methyl-N-(2-phenylimidazo[1,2-a]pyrimidin-7-yl)isonicotinamide A mixture of 2-phenylimidazo[1,2-a]pyrimidin-7-amine (156 mg, 0.766 mmol, 1 eq.), <strong>[4021-11-8]2-methylisonicotinic acid</strong> (116 mg, 0.842 mmol, 1.1 eq.), propylphosphonic anhydride in ethyl acetate 50% (1.13 ml, 1.91 mmol, 2.5 eq) and ethyldiisopropylamine (0.535 ml, 3.06 mmol, 4 eq) in tetrahydrofuran (10 ml) is stirred for 18 hours at roomtemperature. The solution is then refluxed for 4 hours. The mixture is diluted with ethyl acetate and washed with sat. aqueous sodium bicarbonate, with water, dried over magnesium sulfate and the solvent is removed in vacuo. Purification of the residue by chromatography on a 12 g RediSep silica cartridge using dichloromethane+5% methanol as eluent affords 2-methyl-N-(2-phenyl-imidazo[1,2-a]pyrimidin-7-yl)-isonicotinamide (45 mg, 17.8%) as a yellow solid. MS: m/e=330.2 (M+H+) mp.: 255-7 C.
		A mixture of 2-phenylimidazo[l,2-a]pyrimidin-7-amine (156 mg, 0.766 mmol, 1 eq.), 2- methylisonicotinic acid (116 mg, 0.842 mmol, 1.1 eq.), propylphosphonic anhydride in ethyl acetate 50% (1.13 ml, 1.91 mmol, 2.5 eq) and ethyldiisopropylamine (0.535 ml, 3.06 mmol, 4 eq) in tetrahydrofuran (10 ml) is stirred for 18 hours at roomtemperature. The solution is then refluxed for 4 hours. The mixture is diluted with ethyl acetate and washed with sat. aqueous sodium bicarbonate, with water, dried over magnesium sulfate and the solvent is removed in vacuo. Purification of the residue by chromatography on a 12 g RediSep silica cartridge using dichloromethane + 5% methanol as eluent affords 2-methyl-N-(2 -phenyl- imidazo[ 1,2- a]pyrimidin-7-yl)-isonicotinamide (45 mg, 17.8%) as a yellow solid. MS: m/e = 330.2 (M+H+) mp.: 255-7C.

Reference： [1]Patent: US2011/237564,2011,A1 .Location in patent: Page/Page column 37
[2]Patent: WO2011/117264,2011,A1 .Location in patent: Page/Page column 98

7
[ 74840-47-4 ]
[ 591227-12-2 ]
[ 1335299-97-2 ]

Yield	Reaction Conditions	Operation in experiment
30.3%	With N-ethyl-N,N-diisopropylamine;2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; In tetrahydrofuran; ethyl acetate; at 25℃; for 24h;	Example 79 5-Chloro-2-methyl-N-(2-phenylimidazo[1,2-a]pyrimidin-7-yl)pyrimidine-4-carboxamide A mixture of <strong>[74840-47-4]5-chloro-2-methylpyrimidine-4-carboxylic acid</strong> (100 mg, 0.579 mmol), 2-phenylimidazo[1,2-a]pyrimidin-7-amine (146 mg, 0.695 mmol, 1.2 eq), diisopropylethylamine (304 ul, 1.74 mmol, 3 eq) and propylphosphonic anhydride in ethyl acetate 50% (854 ul, 1.45 mmol, 2.5 eq) in tetrahydrofuran (6 ml) is stirred for 1 day at 25 C. The mixture is diluted with ethyl acetate and washed 2 times with water, the organic layer is dried over magnesium sulfate and evapoarted. The crude material was purified by flash chromatography over a 20 g silicagel column using ethyl acetate 100% as eluent to afford 5-chloro-2-methyl-N-(2-phenylimidazo[1,2-a]pyrimidin-7-yl)pyrimidine-4-carboxamide (64 mg, 30.3%) as a yellow solid. MS: m/e=365.1 (M+H+), mp: >250 C.
		A mixture of <strong>[74840-47-4]5-chloro-2-methylpyrimidine-4-carboxylic acid</strong> (100 mg, 0.579 mmol), 2- phenylimidazo[l,2-a]pyrimidin-7-amine (146 mg, 0.695 mmol, 1.2 eq), diisopropylethylamine (304 ul, 1.74 mmol, 3 eq) and propylphosphonic anhydride in ethyl acetate 50 % (854 ul, 1.45 mmol, 2.5 eq) in tetrahydro uran (6 ml) is stirred for 1 day at 25 C. The mixture is diluted with ethyl acetate and washed 2 times with water, the organic layer is dried over magnesium sulfate and evapoarted. The crude material was purified by flash chromatography over a 20 g silicagel column using ethyl acetate 100 % as eluent to afford 5-chloro-2-methyl-N-(2- phenylimidazo[l,2-a]pyrimidin-7-yl)pyrimidine-4-carboxamide (64 mg, 30.3%) as a yellow solid. MS: m/e = 365.1 (M+H+), mp: >250 C

Reference： [1]Patent: US2011/237564,2011,A1 .Location in patent: Page/Page column 37
[2]Patent: WO2011/117264,2011,A1 .Location in patent: Page/Page column 97

8
[ 591227-12-2 ]
[ 62348-13-4 ]
[ 1335298-76-4 ]

Yield	Reaction Conditions	Operation in experiment
16%	With triethylamine; In dichloromethane; at 20℃;	Example 2 Isoxazole-5-carboxylic acid (2-phenyl-imidazo[1,2-a]pyrimidin-7-yl)-amide Triethylamine and 5-ethyl-isoxazole-3-carbonyl chloride were added to a solution of 2-phenyl-imidazo[1,2-a]pyrimidin-7-ylamine (example 1, step 1) in dichloromethane, and the mixture was stirred at RT overnight. The title compound (29 mg, 16%) was isolated from the mixture by preparative HPLC (254 nm, Agilent Zorbax XdB-C18, Run: 7 min, Flow: 30 ml/min, Gradient: 0.0 min: 95/5 H2O/CH3CN; 0.5 min: 95/5 H2O/CH3CN 4.5 min: 5/95 H2O/CH3CN; 6.9 min 5/95 H2O/CH3CN; 7 min 95/5 H2O/CH3CN). MS (m/e)=306.3 [M+H+].

Reference： [1]Patent: US2011/237564,2011,A1 .Location in patent: Page/Page column 19

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H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 591227-12-2 ] {[proInfo.proName]}

Quality Control of [ 591227-12-2 ]

Related Doc. of [ 591227-12-2 ]

Product Details of [ 591227-12-2 ]

Safety of [ 591227-12-2 ]

Application In Synthesis of [ 591227-12-2 ]

[ 591227-12-2 ] Synthesis Path-Downstream 1~8

Precautionary Statements-General

Prevention

Response

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Physical hazards

Health hazards

Environmental hazards

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