2,4-Dichloropyrrolo[2,1-f][1,2,4]triazine

To a co-solvent of diisopropylethylamine (4.5 mL) and toluene (2OmL) was added intermediate 5” (1.6g, 10.4mmoL) and POC13 (2.94mL). The mixture was heated at 120°C in a sealed tube for 20h, then poured into an ice-cooled saturated sodium bicarbonate solution (5OmL). Stirred for 1 5mm. Extracted with CH2C12 (3x5OmL). Combined organic layers were washed with brine (lx5OmL), dried (Mg504) and concentrated. Column chromatography purification (50-100percent CH2C12 in hexanes) afforded the desired dichloride 1 as a light brown solid (1.2g, 86percent yield). ‘H NMR (CDC13): ö 6.98(1H, m), 7.05 (1H, m), 7.86 (1H, m); MS: 187 (M+W).1B. 2, 4-Dichloropyrrolo[1, 2-f][1, 2, 4]triazine; A mixture of 1A (4.7 gm, 31.1 mmol), POCl1B. Step 14) 2, 4-dichloropyrrolor2, l-/iri, 2, 41triazine [0343] To a suspension of pyrrolo[2, l- J[l, 2, 4]triazine-2, 4(lH, 3H)-dione (12.70 g, 84.04 mmol) in toluene (150 mL) were added DIPEA (21.70 g, 0.17 mol) and POCb (38.50 mL, 0.42 mol). The reaction mixture was stirred in a sealed tube at 125 °C for 24 h, then cooled down to rt and poured into a mixture of saturated NaPyrrolo[2, 1-f][1, 2, 4]triazine-2, 4(1H, 3H)-dione (12.70 g, 84.04 mmol) was suspended in toluene(150 mL), and then DIPEA (21.70 g, 0.17 mol) and phosphorus oxychloride (38.50 mL, 0.42 mol) were added to the suspension to obtain a reaction system. The resulting reaction was warmed to 125 ° C, sealed tube reaction 24 hours, and then cooled to room temperature. Then, the reaction system was slowly poured into a mixture of aqueous sodium carbonate (150 mL) and ice (200 g), the organic layer was separated, the aqueous layer was extracted with dichloromethane (200 mL x 5) and the organic layers were combined. The combined organic layers were successively dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was then subjected to silica gel column chromatography (DCM / PE (v / v) = 1/10) to give a yellow oil (11.50 g, 72percent).In a 25mL reaction vial, a mixture of 11 (190mg, 1.3mmol) and POClIntermediate 1-d (190 mg) was added to the flask, And phosphorus oxychloride (2 ml) and diisopropylethylamine (2 ml) were added.The reaction solution was heated to 120 ° C, Nitrogen protection reaction 48h.The reaction was stopped and the reaction solution was allowed to cool to room temperature, The reaction solution was poured into ice, Stir for 5 min.Ethyl acetate (20 ml * 3)And the ethyl acetate layer was dried over anhydrous sodium sulfate, Concentrated to dryness.Column chromatography (petroleum ether: ethyl acetate 8: 1) gave a pale yellow solid (80 mg, 38.3percent).

Molecular Weight:188.01
XLogP3:2.3
Hydrogen Bond Acceptor Count:2
Exact Mass:186.9704025
Monoisotopic Mass:186.9704025
Topological Polar Surface Area:30.2
Heavy Atom Count:11
Complexity:155
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes