ChemicalBook CAS DataBase List PYRROLO[1,2-F][1,2,4]TRIAZIN-4-AMINE

PYRROLO[1,2-F][1,2,4]TRIAZIN-4-AMINE synthesis

10synthesis methods

Product Name:PYRROLO[1,2-F][1,2,4]TRIAZIN-4-AMINE
CAS Number:159326-68-8
Molecular formula:C6H6N4
Molecular Weight:134.14

1-aminopyrrole-2-carbonitrile hydrochloride

937046-97-4

3473-63-0

159326-68-8

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].

109-97-7 Synthesis

109-97-7
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1189-71-5
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$18.00/5g

3473-63-0 Synthesis

3473-63-0
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159326-68-8
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$10.00/250mg

Yield:159326-68-8 1358.6 g

Reaction Conditions:

Stage #1: pyrrole;isocyanate de chlorosulfonyle in N,N-dimethyl-formamide;acetonitrile at 5; for 2.5 h;Large scale;
Stage #2: with O-[4-nitro-2-(trifluoromethyl)phenyl]hydroxylamine in N,N-dimethyl-formamide;acetonitrile at 40 - 80; for 4 h;Large scale;
Stage #3: formamidine acetic acidwith potassium carbonate in N,N-dimethyl-formamide;acetonitrile at 70 - 80; for 5 h;Large scale;Temperature;

Steps:

1-5 Example 3

Add 40L of acetonitrile, 1000g (14.9mol, 1.0eq) of pyrrole, 4218g (29.8mol, 2eq) of chlorosulfonic acid isocyanate into a 100L reactor, stir to dissolve, after dissolution, cool down, when the temperature of the reaction system is 5,Begin to slowly add 1LN,N-dimethylformamide dropwise, keep the temperature for 2.5h,After the incubation, the temperature was raised to 40°C, 4962g (22.4mol, 1.5eq) of O-[4-nitro-2-(trifluoromethyl)phenyl]hydroxylamine was added to the reaction solution, and then the temperature was raised to 80°C , The incubation reaction 4h,After the incubation, add 6198g (59.6mol, 4eq) formamidine acetate and 10kg (74.5mol, 5eq) of potassium carbonate to the system, maintain the temperature at 70 to 80, and keep it for 5h.After keeping warm,Slowly add 10L of water to the reaction system, then concentrate the reaction solution until no liquid drips out, cool to 10°C, stir and crystallize for 5h, wash the filter cake with 10L water, and recrystallize the filter cake with 15L ethyl acetate.Filter and dry the cake, vacuum dry at 451358.6 g of light yellow solid pyrrolo[2,1-F][1,2,4]triazine-4-amine was obtained.

References:

CN111533747,2020,A Location in patent:Paragraph 0030-0031; 0038-0039; 0043-0044; 0048-0049; 0053

3473-63-0 Synthesis

3473-63-0
513 suppliers
$5.00/25g