PYRROLO[1,2-F][1,2,4]TRIAZIN-4-AMINE Chemical Properties

Melting point:

231°

Density 

1.50

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

pka

4.28±0.30(Predicted)

form 

powder

color 

Light brown

InChI

InChI=1S/C6H6N4/c7-6-5-2-1-3-10(5)9-4-8-6/h1-4H,(H2,7,8,9)

InChIKey

VSPXQZSDPSOPRO-UHFFFAOYSA-N

SMILES

N12C=CC=C1C(N)=NC=N2

Safety Information

Hazard Codes 

T

Risk Statements 

25

Safety Statements 

45

RIDADR 

UN2811

HS Code 

2933698090

PYRROLO[1,2-F][1,2,4]TRIAZIN-4-AMINE Usage And Synthesis

Uses

Pyrrolo[2,1-F][1,2,4]triazine-4-amine (an intermediate for remdesivir) is used in the synthesis of the drug remdesivir.

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 31, p. 781, 1994 DOI: 10.1002/jhet.5570310415

Synthesis

To a stirred suspension of 1-amino-1H-pyrrole-2-carbonitrile hydrochloride (50 g, 0.35 mol) in anhydrous ethanol (800 mL) was sequentially added formamidine acetate (181.3 g, 1.74 mol) and potassium phosphate (370 g, 1.74 mol). The reaction mixture was heated to 78 °C under nitrogen protection and maintained for 18 hours. After completion of the reaction, it was cooled to room temperature, the reaction mixture was filtered and the filtrate was concentrated to dryness under vacuum. The residue was mixed with ice water (2 L) and the resulting dark gray-brown solid was collected by filtration. The filter cake was washed with water, blotted dry, the solid was dissolved in hot ethyl acetate and filtered over a funnel into a collection vessel. The resulting dark solution was filtered through a 30/40 Magnesol long stopper, and the light yellow filtrate was collected and concentrated to dryness under vacuum to give a yellow solid product (20.6 g, 44.1% yield). The Magnesol plug was washed with ethyl acetate/ethanol and the washings were concentrated under vacuum to give additional product (10.7 g, 23%). The aqueous phase filtrate was extracted with ethyl acetate and the organic phase was dried, Magnesol filtered and concentrated to give a further purified product (6.3 g, 14%), bringing the total yield to 37.6 g (81%). The product was characterized by 1H-NMR (CD3OD) and LC/MS (+ESI): 1H-NMR δ 7.72 (s, 1H), 7.52 (dd, 1H, J = 2.5, 1.6 Hz), 6.85 (dd, 1H, J = 4.5, 1.6 Hz), 6.64 (dd, 1H, J = 4.5, 2.7 Hz); LC/MS m/z = 135.1 [M + H].

References

[1] Patent: WO2007/56170, 2007, A2. Location in patent: Page/Page column 73-74
[2] Patent: WO2007/64931, 2007, A2. Location in patent: Page/Page column 163

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