6-Bromo-4-quinazolinamine

Ammonia gas was bubbled through a solution of 6-bromoisotoic anhydride (2 g, 8.26 mmol) in DMF (20 mL) at r.t. for 15 min. The solution was then degassed by bubbling nitrogen into the solution for 5 min also removing (NHGeneral procedure: Method A: Benzonitriles were suspended in formamide (40 equiv) and InClPlace Add 6-bromo-4-chloroquinazoline (1 g, 5.02 mmol) to a 50 mL round bottom flask, After adding 15mL of tetrahydrofuran to stir and dissolve, add ammonia water (1.7mL, 100mmol) to the system, increase the temperature to 40 C and reflux for 5h. The reaction was monitored by TLC.The reaction was stopped and a solid precipitated in the system. Cool to room temperature, suction filter, wash with water, After drying, 0.8 g of a pale yellow solid was obtained with a yield of 88.6%.A mixture of compound 13-a (114.1 mg, 0.54 mmol), To a stirred solution of compound 9A (reference: US 2009/0163489 Al) (0.3 15 g, 1.24 mmol) and 2-chloro-3-(4, 4, 5 , 5 -tetramethyl- 1, 3 , 2-dioxaborolan-2-yl)pyridine (Reference WO 2015157093 Al/WO 2015044172 Al/WO 2014055955 Al) (0.445, 1.86 mmol) in 1, 4- dioxane (9 mL) and water (3 mL) was added Na2CO3 (0.3 94 g, 3.72 mmol). The reaction mixture was degassed for 3 mm. and then to it was added Pd(PPh3)4 (0. 143g, 0.124 mmol), and the resultant mixture was heated at 100 C for 12 h. The reaction mixture was then filtered through a Celite pad, the filter cake washed with ethyl acetate and the combined filtrate evaporated under reduced pressure to give the cmde compound. It was purified via silica gel chromatography (24 g Redisep column, eluted with 60 % ethyl acetate in petroleum ether) to furnish N-(6-(2-chloropyridin-3-yl)imidazo[ 1 , 2-ajpyridin-2-yl)acetamide 9B (211 mg, 0.736 mmol, 59.4 % yield) as a light yellow solid. LCM5: m/z = 385.0 [M+Hf?; ret. time 1.49 mm; condition C. Compound 19B was synthesized by reacting 19A (reference: Angew. Chem. mt. Ed. 2014, 53, 305-309) and 2-chloro-3-(4, 4, 5, 5-tetramethyl-1 , 3, 2-dioxaborolan-2-yl)pyridine employing the experimental procedure described for compound 9B as shown in Scheme 16. The crude residue was purified by silica gel chromatography (40 g RediSep column, eluting with a gradient of 35% ethyl acetate in petroleum ether) to yield 6-(2-chloropyridin-3- yl)quinazolin-4-amine 18B (0.6g, 2.337 mmol, 52.4 % yield). LCMS: m/z = 257.2 [M+Hf?; ret. time 1.06 mm; condition E.

Molecular Weight:224.06
XLogP3:2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Exact Mass:222.97451
Monoisotopic Mass:222.97451
Topological Polar Surface Area:51.8
Heavy Atom Count:12
Complexity:164
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes