Triacetoxyperiodinane → 6-Bromo-2-methylpyrimidine-4-carbaldehyde

To a cold solution of (6-bromo-2-methylpyrimidin-4-yl)methanol (15 g, 73.9 mmol, Preparation #4) in DCM (300 mL) was added Dess-Martin periodinane (47.0 g, 111 mmol). The resulting suspension was allowed to warm to RT and stirred for about 2 h. The reaction mixture was re-cooled to about 0° C., quenched with sodiumthiosulphate solution (200 mL) and stirred vigorously for about 30 min. The organic layer was separated and washed successively with saturated sodium bicarbonate (2×200 mL), water (1×200 mL) and brine (1×200 mL). The organic layer was dried over sodium sulphate and concentrated under reduced pressure to afford 6-bromo-2-methylpyrimidine-4-carbaldehyde 11 g (74.1%), 1H NMR (400 MHz, DMSO) δ: 9.88 (s, 1H), 7.96 (s, 1H), 2.73 (s, 3H), IR Neat 1720 (C═O) cm−1

1. temperatureThe reaction mixture was re-cooled to about 0° C.
2. customquenched with sodiumthiosulphate solution (200 mL)
3. stirringstirred vigorously for about 30 min
4. customThe organic layer was separated
5. washwashed successively with saturated sodium bicarbonate (2×200 mL), water (1×200 mL) and brine (1×200 mL)
6. dry with materialThe organic layer was dried over sodium sulphate
7. concentrationconcentrated under reduced pressure

ORD record

ord-fbf16991433a4b92958de7b716a0c201

Source dataset

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09029409B2