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2-AMINO-5-CYANOPYRAZINE

2-AMINO-5-CYANOPYRAZINE structure

CAS No:
113305-94-5
Formula:
C5H4N4
Chemical Name:
2-AMINO-5-CYANOPYRAZINE
Synonyms:
IFLAB-BB F2108-0176;5-AMINOPYRAZINE-2-CARBONITRILE;2-AMINO-5-CYANOPYRAZINE;5-amino-5-cyanopyrazine;2-AMINO-5-CYANOPYRAZINE, 95+%;5-AMINO-2-CYANOPYRAZINE;Pyrazinecarbonitrile, 5-amino-
Categories:
Pharmaceutical Intermediates > Heterocyclic Compound

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2-AMINO-5-CYANOPYRAZINE Basic Attributes

Molecular Weight：

120.11

Exact Mass：

120.043594

DSSTox ID：

DTXSID30552582

Characteristics

PSA：

75.6

XLogP3：

-0.4

Density：

1.34±0.1 g/cm3(Predicted)

Boiling Point：

366.8±42.0 °C(Predicted)

Flash Point：

175.6±27.9 °C

Refractive Index：

1.600

Vapor Pressure：

0mmHg at 25°C

Safety Information

Hazard category：

IRRITANT

hazard class code：

safety instructions：

26-39

Precautionary statement(s)：

P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P403+P233, P405, P501

Hazard Statements：

H302

GHS Classification：

|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 3 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

2-AMINO-5-CYANOPYRAZINE Use and Manufacturing

5-bromopyrazine-2-carbonitrile; i) Tetrakis (triphenyl phosphine) palladium(0) (10 mg) was added to a mixture of 5-bromopyrazin-2-amine (0.575 mmol), potassium cyanide (1.15 mmol), copper (I) iodide (0.575 mmol) and 18-crown-6 (20 mg) in dry DMF (1 mL) in a screw top reaction vessel under nitrogen atmosphere, and the mixture was heated with stirring at 200° C. for 1 h. After cooling, water (5 mL) was added and the product was extracted with chloroform (2.x.) to give 5-aminopyrazine-2-carbonitrile after purification by chromatography (silica, hexane:ethyl acetate) (0.208 mmol, 36percent).EXAMPLE 1B Step 1: To 5-bromo-pyrazin-2-ylamine (0.46 g, 2.6 mmol), NaCN (1.3 g, 26 mmol) and CuCN (2.74 g, 26 mmol) in a nitrogen-purged vial was added DMF (10 mL). The resulting mixture was heated at 120° C. over the weekend. After cooling down to room temperature, DMF was removed under high vacuum. The residue was partitioned between EtOAc and water. The organic extracts were combined, dried and concentrated to give the crude product as a yellow solid (0.296 g, 93percent), which was used in the subsequent reaction without further purification.Example 645-[3-Hydroxy-5-(1H-indol-4-yl)-phenylamino]-pyrazine-2-carbonitrileTo 5-bromo-pyrazin-2-ylamine (0.46 g, 2.6 mmol), NaCN (1.3 g, 26 mmol) and CuCN (2.74 g, 26 mmol) in a nitrogen-purged vial was added DMF (10 mL). The resulting mixture was heated at 120° C. over the weekend. After cooling down to room temperature, DMF was removed under high vacuum. The residue was partitioned between EtOAc and water. The organic extracts were combined, dried and concentrated to give the crude product as a yellow solid (0.296 g, 93percent), which was used in the subsequent reaction without further purification.The Buchwald reaction was carried out as described above and the product was converted to 5-[3-hydroxy-5-(1H-indol-4-yl)-phenylamino]-pyrazine-2-carbonitrile as described for Example 35. [0336] To 5-bromo-pyrazin-2-ylamine (0.46 g, 2.6 mmol), NaCN (1.3 g, 26 mmol) and CuCN (2.74g, 26 mmol) in a nitrogen-purged vial was added DMF (10 mL). The resulting mixture was heated at 12O19.1. 5-chloro-3- (cyclohex-1-en-1-yl) -7-methoxy-6- (4-methoxyphenyl) -2-phenylpyrazolo [1, 5-a] pyrimidine (500 mg, 1.07 mmol) , Intermediate 5 (500 mg, 1.13 mmol) ,

Computed Properties

Molecular Weight:120.11
XLogP3:-0.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Exact Mass:120.043596145
Monoisotopic Mass:120.043596145
Topological Polar Surface Area:75.6
Heavy Atom Count:9
Complexity:135
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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