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2-Pyrazinemethanol

2-Pyrazinemethanol structure

CAS No:
6705-33-5
Formula:
C5H6N2O
Chemical Name:
2-Pyrazinemethanol
Synonyms:
2-Pyrazinemethanol;Pyrazinemethanol;2-(Hydroxymethyl)pyrazine;(Hydroxymethyl)pyrazine;Pyrazin-2-ylmethanol
Categories:
Pharmaceutical Intermediates > Heterocyclic Compound

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2-Pyrazinemethanol Basic Attributes

Molecular Weight：

110.11

Exact Mass：

110.11

UNII：

C27Z7QI77D

DSSTox ID：

DTXSID00217338

HScode：

2933990090

Characteristics

PSA：

XLogP3：

-1

Density：

1.2±0.1 g/cm3

Melting Point：

38.5

Boiling Point：

64-66 °C @ Press: 0.3 Torr

Flash Point：

94.1±23.2 °C

Refractive Index：

1.557

Safety Information

hazard class code：

36/37/38-41-37/38-22

safety instructions：

26-36/37/39-24/25-39

RTECS Number：

UQ3625000

Marks：

Xi,Xn

Hazard note：

Irritant

Precautionary statement(s)：

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

Hazard Statements：

H315

GHS Classification：

|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 3 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

2-Pyrazinemethanol Use and Manufacturing

The 4- (3-CHLORO-4- (2-PYAZINYLMETHOXY) anilino) -5-fluoroquinazoline used as starting material was obtained as follows: Methylpyrazine carboxylate (8.5g) was stirred in water (200 ml) and sodium borohydride (11.65 g) was added in one portion, resulting in a vigorous exotherm. The reaction mixture was stirred vigorously for 30 minutes, and then ethanol (80 ML) and saturated potassium carbonate (150 ml) were added. The mixture was stirred for 30 minutes and then extracted with ethyl acetate (5 x 150 ml) and DCM (5 x 150 ml). The combined extracts were dried and concentrated to give pyrazin-2-ylmethanol as a yellow oil (5.43 g, 80percent), which was used without purification; NMR spectrum (DMSO-D6) 4.65 (s, 2H), 5.57 (br s, 1H), 8.54 (d, 2H), 8.71 (s, 1H).To methyl pyrazine-2-carboxylate (3.35 g, 24.3 mmol) in EtOH (60 mL) was added calcium chloride (4.03 g, 36.4 mmol) followed by sodium borohydride (1.38 g, 36.4 mmol). The reaction mixture was stirred at 23°C for 5 h. The mixture was quenched with a mixture of acetic acid (4.20 mL, 72.8 mmol) and water (1.31 mL, 72.8 mmol), and stirred for 30 min. The mixture was filtered through a pad a silica gel, and the pad was washed with 5-10percent MeOH/DCM containing 0.3percent conc. NHStep 2; Lithium aluminum hydride (40.0 mg, 1.06 mmol) was suspended in tetrahydrofuran (1.0 mL). To this, a solution of methyl 2-pyrazinecarboxylate (66.0 mg, 0.478 mmol) in tetrahydrofuran (0.5 mL) was added dropwise under a nitrogen atmosphere at 0° C. and the mixture was stirred at the same temperature for 15 minutes. Then, water (40 μL), a 15percent aqueous sodium hydroxide solution (40 μL) and water (120 μL) were successively added to the reaction mixture and the mixture was stirred at room temperature for 1 hour. The mixture was filtered through Celite and the mother liquid was concentrated. The residue was purified by silica gel column chromatography (chloroform/methanol=9/1) to give 2-pyrazinemethanol (Compound CD) (19.0 yield: 36percent).[0537] Synthesis of pyrazin-2-ylmethanol: [0538] To a stirred solution of methyl pyrazine-2-carboxylate (0.5 g, 3.62 mmol) in HTo a neat mixture of 3-(3-((6-fluoropyridin-3-yl)methyl)isoxazol-5-yl)pyridin-2 -amine (Intermediate E, 50 mg, O. l9mmol) and

Computed Properties

Molecular Weight:110.11
XLogP3:-1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:110.048012819
Monoisotopic Mass:110.048012819
Topological Polar Surface Area:46
Heavy Atom Count:8
Complexity:67.4
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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