[ CAS No. 5453-07-6 ]

Name: 5453-07-6|5-Amino-3-methyl-1H-pyrazole-4-carbonitrile|98%
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Product Details of [ 5453-07-6 ]

CAS No. :	5453-07-6	MDL No. :	MFCD02020550
Formula :	C₅H₆N₄	Boiling Point :	429.4°C at 760 mmHg
Linear Structure Formula :	-	InChI Key :	-
M.W :	122.13 g/mol	Pubchem ID :	227460
Synonyms :

Safety of [ 5453-07-6 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338-P310	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 5453-07-6 ]

Upstream synthesis route of [ 5453-07-6 ]
Downstream synthetic route of [ 5453-07-6 ]

[ 5453-07-6 ] Synthesis Path-Upstream 1~4

1
[ 5417-82-3 ]
[ 5453-07-6 ]

Yield	Reaction Conditions	Operation in experiment
60%	at 20℃; Reflux	5-amino-3-methyl-lH-pyrazole-4-carbonitrile [00148] Hydrazine hydrate (4.5 mL, 92 mmol) was placed in a 50 mL round bottom flask. While stirring at rt, (l-ethoxyethylidene)malononitrile (5.0 g, 37 mmol) was added in portions. After half the material had been added, the flask was placed in an ice-water bath. Upon completion of addition, a precipitate had begun to form and the reaction flask was removed from the ice-water bath and heated at reflux for 2h, then cooled to rt. The resulting solution was briefly cooled in an ice-water bath and then sonicated for a few moments to induce crystallization. Solids were collected by filtration, washed with water and then dried in vacuo to give 5-amino-3-methyl-lH-pyrazole-4-carbonitrile (2.69 g. 60percent). 1H MR (300 MHz, d₆- DMSO) 6 3.31 (s, 3H).
51%	With hydrazine In ethanol at 0 - 80℃;	Step 2: 5-amino-3-methyl-1H-pyrazole-4-carbonitrile To a solution of hydrazine H₂NNH₂(3.7 g, 74 mmol) in EtOH (5 mL), 2-(1-ethoxy-ethylidene)-malononitrile (5.0 g, 37 mmol) was added in portion at 0° C. Then the mixture was heated to 80° C. for 1.5 hrs. Then the mixture was cooled to room temperature, added H₂O, cooled with ice/water bath and filtered to give 5-amino-3-methyl-1H-pyrazole-4-carbonitrile (2.3 g, yield 51percent) as a yellow solid.
8 g	With hydrazine hydrate In ethanol at 95℃; for 3 h;	To a solution of 2-(l-ethoxyethylidene)propanedinitrile (17 g, crude) in ethanol (100 ml) was added N₂H₄H₂O (11.6 g, 185.60 mmol), and the reaction mixture was stirred for 3 h at 95°C in an oil bath. The resulting mixture was concentrated in vacuo to give a residue, which was purified by silica gel column chromatography with 2 percent to 10 percent methanol in dichloromethane to afford 5-amino-3-methyl-lH- pyrazole-4-carbonitrile as a white solid (8 g). LC/MS (ES, m/z):[M+H]⁺ 123.1.

Reference： [1] Patent: WO2018/89786, 2018, A1, . Location in patent: Paragraph 00148
[2] Patent: US2012/202785, 2012, A1, . Location in patent: Page/Page column 259
[3] Journal of Organic Chemistry, 1956, vol. 21, p. 1240,1242
[4] Bioorganic and Medicinal Chemistry Letters, 2000, vol. 10, # 8, p. 821 - 826
[5] Patent: US2006/135526, 2006, A1, . Location in patent: Page/Page column 21
[6] Patent: US2009/48274, 2009, A1, . Location in patent: Page/Page column 6
[7] Patent: WO2014/66795, 2014, A1, . Location in patent: Paragraph 0175
[8] Beilstein Journal of Organic Chemistry, 2014, vol. 10, p. 2338 - 2344
[9] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 14, p. 3201 - 3204

2
[ 1202180-98-0 ]
[ 5453-07-6 ]

Reference： [1] Journal of Combinatorial Chemistry, 2010, vol. 12, # 1, p. 69 - 74

3
[ 2644-70-4 ]
[ 5515-16-2 ]
[ 5453-07-6 ]

Reference： [1] Chemical Biology and Drug Design, 2014, vol. 84, # 3, p. 270 - 281

4
[ 1187-11-7 ]
[ 5453-07-6 ]

Reference： [1] Chemical Biology and Drug Design, 2014, vol. 84, # 3, p. 270 - 281

[ 5453-07-6 ] Synthesis Path-Downstream 1~12

1
[ 5453-07-6 ]
[ 610-14-0 ]
[ 83451-26-7 ]
[ 83451-31-4 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In chloroform for 3h; Heating; Yield given. Yields of byproduct given;

Reference： [1]Plescia; Daidone; Bajardi [Journal of Heterocyclic Chemistry, 1982, vol. 19, # 3, p. 685 - 687]

2
[ 5453-07-6 ]
[ 165328-10-9 ]
2-methyl-5-(4-trifluoromethyl-phenyl)-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine-3-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	In acetic acid for 3.5h; Heating / reflux;	2.1 Example 2: Preparation of phenyl-7-trifluoromethyl-pyrazolo [1, 5-a] pyrimidine-3- carbonitriles (General Procedure B); A stirred mixture of commercially available 3-amìno-4-cyano-5-methyl-pyrazole (1 eq. ) and a 1-phenyl-4, 4, 4-trifluoro-butane-1, 3-dione (1 eq. ), prepared according to general procedure A, in acetic acid was heated under reflux conditions for about 3.5 h. The reaction mixture was evaporated and the product was isolated by column chromatography (heptane/ethyl acetate) and further purified by crystallization. If the product precipitates during the reaction it can be isolated by filtration and further purified by crystallization; Example 2.1 2-Methyl-5- (4-trifluoromethyl-phenyl)-7-trifluoromethyl-pyrazolo [1, 5-a] pyrimidine-3- carbonitrile; Reaction of 1- (4-trifluoromethyl-phenyl)-4, 4, 4-trifluoro-butane-1, 3-dione (284 mg, 1.0 mmol), prepared from commercially available 4-trifluoromethyl-acetophenone according to general procedure A, and commercially available 3-amino-4-cyano-5- methyl-pyrazole (122 mg, 1. 0 mmol) according to general procedure B yielded the title compound as a light yellow solid (234 mg, 63%). MS (ISP) 371.1 [(M+H)+] ; mp 184°C

Reference： [1]Current Patent Assignee: ROCHE HOLDING AG - WO2005/40171, 2005, A1 Location in patent: Page/Page column 32

3
1-N,N-dimethylamino-3-(2,5-dichlorophenyl)-3-oxo-1-propene [ No CAS ]
[ 2476-37-1 ]
[ 5453-07-6 ]
[ 4637-24-5 ]
[ 115955-47-0 ]

Yield	Reaction Conditions	Operation in experiment
	In acetic acid	2 7-(2,5-Dichlorophenyl)-2-methylpyrazolo(1,5-a)-pyrimidine-3-carboxamide EXAMPLE 2 7-(2,5-Dichlorophenyl)-2-methylpyrazolo(1,5-a)-pyrimidine-3-carboxamide A mixture of 31.0 g of 2',5'-dichloroacetophenone and 25 ml of N,N-dimethylformamide dimethyl acetal is heated on a steam bath for 6 hours, then evaporated to dryness in vacuo. The residue is slurried with hexane, filtered, and gives 35.3 g of 2', 5'-dichloro-3-dimethylaminoacrylophenone as orange crystals, mp 83-85° C. A mixture of 12.2 g of 3-amino-4-cyano-5-methylpyrazole and 24.4 g of 2',5'-dichloro-3-dimethylaminoacrylophenone in 250 ml of glacial acetic acid is heated on a steam bath for 4 hours. The mixture is cooled and filtered and gives 21.28 g of 7-(2,5-dichlorophenyl)- 2-methyl-pyrazolo(1,5-a)pyrimidine-3-carbonitrile as off-white crystals.

Reference： [1]Current Patent Assignee: PFIZER INC - US5013737, 1991, A

4
1-N,N-dimethylamino-3-(2,5-dichlorophenyl)-3-oxo-1-propene [ No CAS ]
[ 5453-07-6 ]
[ 115955-47-0 ]

Yield	Reaction Conditions	Operation in experiment
	In acetic acid	6 7-(2,5-Dichlorophenyl)-2-methylpyrazolo(1,5-a-) pyrimidine-3-carboxamide A mixture of 12.2 g of 3-amino-4-cyano-5-methyl-pyrazole and 24.4 g of 2',5'-dichloro-3-dimethylaminoacrylophenone in 250 ml of glacial acetic acid is heated on a steam bath for 4 hours. The mixture is cooled and filtered to give 21.28 g of 7-(2,5-dichlorophenyl)-2-methylpyrazolo(1,5-a)pyrimidine-3-carbonitrile as off-white crystals.
	In acetic acid	2 7-(2,5-Dichlorophenyl)-2-methylpyrazolo[1,5-a]pyrimidine-3-carboxamide A mixture of 12.2 g of 3-amino-4-cyano-5-methylpyrazole and 24.4 g of 2',5'-dichloro-3-dimethylaminoacrylophenone in 250 ml of glacial acetic acid was heated on a steam bath for 4 hours. The mixture was cooled and filtered and gave 21.28 g of 7-(2,5-dichlorophenyl)-2-methylpyrazolo[1,5-a]pyrimidine-3-carbonitrile as off-white crystals.

Reference： [1]Current Patent Assignee: PFIZER INC - US5059691, 1991, A
[2]Current Patent Assignee: MCCORMICK PATRICK; PFIZER INC - US4847256, 1989, A

5
[ 5453-07-6 ]
(E)-3-(dimethylamino)-1-(pyridin-3-yl)prop-2-en-1-one [ No CAS ]
2-methyl-7-(pyridin-3-yl)pyrazolo[1,5-a]pyrimidine-3-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In hexane; dichloromethane; acetic acid	39 2-Methyl-7-(3-pyridyl)pyrazolo[1,5-a]pyrimidine-3-carbonitrile EXAMPLE 39 2-Methyl-7-(3-pyridyl)pyrazolo[1,5-a]pyrimidine-3-carbonitrile A mixture of 3.50 g. of 3-dimethylamino-1-(3-pyridyl)-2-propen-1-one, 25 L ml. of glacial acetic acid and 2.44 g. of 3-amino-5-methylpyrazole-4-carbonitrile is refluxed 6 hours. The solvent is removed in vacuo. The residue is dissolved in dichloromethane and the solution washed with saturated sodium bicarbonate solution. The dichloromethane layer is dried over anhydrous sodium sulfate and pased through a column of hydrous magnesium silicate. The eluent is concentrated and hexane added to give 2.60 g. of the product of the example, m.p. 245°-246° C.

Reference： [1]Current Patent Assignee: PFIZER INC - US4281000, 1981, A

6
3-dimethylamino-2-methyl-1-(pyridin-3-yl)-2-propen-1-one [ No CAS ]
[ 5453-07-6 ]
2,6-dimethyl-7-(pyridin-3-yl)pyrazolo[1,5-a]pyrimidine-3-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In hexane; acetic acid	40 2,6-Dimethyl-7-(3-pyridyl)pyrazolo[1,5-a]pyrimidine-3-carbonitrile EXAMPLE 40 2,6-Dimethyl-7-(3-pyridyl)pyrazolo[1,5-a]pyrimidine-3-carbonitrile A mixture of 1.90 g. of 3-dimethylamino-2-methyl-1-(3-pyridyl)-2-propen-1-one and 1.22 g. of 3-amino-5-methylpyrazole-4-carbonitrile in 25 ml. of glacial acetic acid is refluxed for 6 hours. The solvent is removed in vacuo and the residue partitioned between dichloromethane and saturated sodium bicarbonate solution. The dichloromethane layer is separated, dried over anhydrous sodium sulfate and passed through a column of hydrous magnesium silicate. The eluent is concentrated and hexane added to give 0.95 g. of the product of the example, m.p. 207°-209° C.

Reference： [1]Current Patent Assignee: PFIZER INC - US4281000, 1981, A

7
[ 5417-82-3 ]
[ 5453-07-6 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrazine hydrate In ethanol; water for 1h; Cooling; Reflux;	4.1. General procedure Pyrazoles (1, 2) were prepared by adding ethoxymethylenemalonitrile or methylethoxymethylenemalonitrile to aq. hydrazine hydrate (35%) in ethanol with cooling, which was followed by refluxing for 1 h. After cooling, the resulting solid was collected by filtration and recrystallized from water (1) or acetonitrile (2) [30].

Reference： [1]Location in patent: experimental part Emelina, Elena E.; Petrov, Alexander A.; Borissova, Alexandra O.; Filyukov, Dmitriy V.; Antipin, Mikhail Yu. [Journal of Molecular Structure, 2012, vol. 1014, p. 63 - 69]

8
[ 81581-27-3 ]
[ 5453-07-6 ]
[ 1607023-81-3 ]

Yield	Reaction Conditions	Operation in experiment
75%	With toluene-4-sulfonic acid; In butan-1-ol; at 130.0℃; for 48h;	To a solution of 5-amino-3-methyl-lH-pyrazole-4-carbonitrile (500 mg, 4.09 mmol) in n-BuOH (4 ml) was added 4-methylbenzene-l -sulfonic acid (27 mg, 0.16 mmol), ethyl 3-(2H-l ,3-benzodioxol-5-yl)-3-oxopropanoate (1.1 g, 4.66 mmol), and the reaction mixture was stirred for 2 days at 130C in an oil bath. The solids were collected by filtration and washed with methanol (15 ml) to afford 5-(2H-l ,3- benzodioxol-5-yl)-2-methyl-7-oxo-4H,7H-pyrazolo[l,5-a]pyrimidine-3-carbonitrile as a gray solid (900 mg, 75 ). LC/MS (ES, m/z):[M+H]+ 295.1 *H NMR (300 MHz, DMSO) delta 13.28 (s, 1H), 7.37 - 7.44 (m, 2H), 7.10 (d, / = 8.1 Hz, 3H), 6.18 (s, 1H), 6.16 (s, 2H), 2.40 (s, 3H)

Reference： [1]Patent: WO2014/66795,2014,A1 .Location in patent: Paragraph 0175

9
[ 2644-70-4 ]
[ 5515-16-2 ]
[ 5453-07-6 ]

Reference： [1]Chemical Biology and Drug Design,2014,vol. 84,p. 270 - 281

10
[ 5453-07-6 ]
[ 479630-08-5 ]
tert-butyl 4-(3-cyano-2-methyl-5-oxo-4,5-dihydropyrazolo[1,5-a]pyrimidin-7-yl)piperidine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62.2 mg	With potassium phosphate at 180℃; for 0.25h; Microwave irradiation;	18A Example 18A Tert-butyl 4-(3-cyano-2-methyl-5-oxo-4,5-dihydropyrazolo[l,5-a]pyrimidin-7-yl)piperidine-l-carboxy- late Tert-butyl 4-(3-ethoxy-3-oxopropanoyl)piperidine-l -carboxylate (1.00 g, 3.34 mmol, 1.5 eq), 3-amino- 5-methyl-lH-pyrazole-4-carbonitrile (272 mg, 2.27 mmol, 1 eq) and potassium phosphate (945 mg, 4.45 mmol, 2 eq) were suspended in l-methoxy-2-propanol (6.5 mL) in a 20 mL microwave vial. The vial - - was capped and the mixture was heated in a microwave to 180°C for 15 min. After cooling to RT, the mixture was evaporated in vacuo, diluted with water (5 mL), adjusted to pH 7 with IN HC1 and extracted with ethyl acetate (3x10 mL). The combined organic layers were dried with sodium sulfate, filtered and evaporated in vacuo. The residue was purified by preparative HPLC (Method 1A). The combined product fractions were adjusted to pH 7 by addition of aqueous ammonium hydroxide. Acetonitrile was evaporated in vacuo, the resulting suspension was filtered, the residue was washed with water (0.5 mL) and dried for 16 h at 50°C in vacuo to give the title compound (62.2 mg, 8% of theory). LC-MS (Method IB): Rt = 0.96 min, MS (ESINeg): m/z = 356 [M-H]"

Reference： [1]Current Patent Assignee: BAYER AG - WO2016/71216, 2016, A1 Location in patent: Page/Page column 161-162

Yield	Reaction Conditions	Operation in experiment
	With hydrazine hydrate In ethanol at 80℃; for 3h;	9.2 Embodiment 2:3 - amino -4 - cyano pyrazole (intermediate 2 a) preparation of General procedure: In a 250 ml round bottom flask is added 2 - (methoxy methylene) malononitrile (1.08 g, 10 mmol), for 100 ml ethanol after completely dissolved, slowly dropping water gathers jing (485 μl, 30 mmol), after dropping the reaction liquid in the 80 °C stirring 3 h. After the reaction, cooling to room temperature, the solvent is removed by distillation under reduced pressure, to obtain the solid crude product, the residue is dissolved in 50 ml DCM dissolved, coils, column chromatography purification, the eluant (PE) selected petroleum ether: ethyl acetate (EA)=3:1, to obtain white solid 872 mg, yield 80.7%.

12
[ 5453-07-6 ]
[ 1211522-68-7 ]

Reference： [1]Patent: KR2018/137057,2018,A

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P502	Refer to manufacturer/supplier for information on recovery/recycling

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
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. 5453-07-6 ]

Quality Control of [ 5453-07-6 ]

Related Doc. of [ 5453-07-6 ]

Product Details of [ 5453-07-6 ]

Safety of [ 5453-07-6 ]

Application In Synthesis of [ 5453-07-6 ]

[ 5453-07-6 ] Synthesis Path-Upstream 1~4

[ 5453-07-6 ] Synthesis Path-Downstream 1~12

Related Functional Groups of [ 5453-07-6 ]

Nitriles

Amines

Related Parent Nucleus of [ 5453-07-6 ]

Pyrazoles

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 5453-07-6 ]

Related Parent Nucleus of
[ 5453-07-6 ]