5-Bromo-N,N-dimethyl-2-pyrazinamine

2-Amino-5-bromo-pyrazine (20) (1, 170mg, 6.72mmol), was dissolved in iodomethane (CH3I) (1.2ml, 19.5mmol) in tetrahydrofuran (THF) (100ml). The solution was cooled to 0 ° C., 60percent sodium hydride (NaH) (1.5g, 37.5mmol) was added slowly and the mixture was stirred for 5 hours. A small amount of methanol was added to the reaction mixture, an excess of iodomethane, to decompose sodium hydride. Followed by water (10ml) was added and extracted with ethyl acetate (3 × 200ml). The organic layers were combined, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by column chromatography [silica gel 48.5 g; hexane - ethyl acetate (1: 1)] and purified by, 2-dimethylamino-5-bromo-pyrazine (21) (1, 096mg, 5.4mmol , 80percent) as a pale yellow powdered solid.2-dimethylamino-5-bromo-pyrazine (21) (1.37g, 6.8mmol) was dissolved in dehydrated tetrahydrofuran (THF) (50ml), it was under an argon atmosphere. The solution was cooled to -80 C. with acetone bath, 1.57 M n-butyl lithium (n-BuLi) slowly added hexane solution (10.8 ml), and stirred for 1 hour. Then it was slowly added N, N-dimethylformamide (DMF) (2.0ml, 26mmol) to this mixed solution was stirred for 1 h allowed to warm to room temperature. Then stirred for 15 minutes Water was added to the reaction mixture and extracted with ethyl acetate (2 × 200ml). The organic layers were combined, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography [silica gel 46.9g; hexane - ethyl acetate (1: 1)] and purified by, 5-aldehyde-2-dimethyl-amino-pyrazine (22) (975mg, 6.5mmol, 95 %) as a light yellow powder solid.To asolution of dimethyl amino 3d (1370 mg, 6.82mmol) in drytetrahydrofuran (50 mL) under Ar at 80 C was slowly added1.57M n-butyllithium hydride (n-BuLi) in hexane (10.8 mL).After stirring for 60min at 80 C, to the mixture was addedN, N-dimethylformamide (DMF) (2.0 mL, 26mmol) and theresulting solution was allowed to warm to r.t. After stirring for1 h, to the reaction mixture was added water to decompose theexcess reducing agent. Further, to the mixed solution was addedwater followed by extraction with ethyl acetate (3 200 mL).The combined organic layers were dried over Na2SO4, filtered, and the solvents were removed under reduced pressure. Theresidue obtained was purified by silica gel column chromatography(hexane/ethyl acetate = 1/1) to yield arylaldehyde 4d (975 mg, 6.46mmol, 95%) as a light yellow solid: mp 112 C;IR (neat, , cm1): 2783, 1681, 1373, 1008; 1HNMR (500MHz, CDCl3) 9.91 (s, 1H), 8.69 (s, 1H), 8.08 (d, J = 1.1 Hz, 1H), 3.26 (s, 6H); 13CNMR (126 MHz, CDCl3) 190.7, 155.5, 144.3, 136.8, 129.4, 37.9; HR-ESI-MS: m/z: [M+ H]+ calculatedfor C7H10N3O, 152.0824; found, 152.0814.

Molecular Weight:202.05
XLogP3:1.8
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:200.99016
Monoisotopic Mass:200.99016
Topological Polar Surface Area:29
Heavy Atom Count:10
Complexity:107
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes