Hydroxyamine hydrochloride → 6-Bromo-2-methylpyrimidine-4-carbaldehyde oxime

HRID 572677

Reaction equation

[Br:1][C:2]1[N:7]=[C:6]([CH3:8])[N:5]=[C:4]([CH:9]=O)[CH:3]=1.[NH2:11][OH:12].Cl.C([O-])(=O)C.C(O)(=O)C.[Na+]>C(O)C.O>[Br:1][C:2]1[N:7]=[C:6]([CH3:8])[N:5]=[C:4]([CH:9]=[N:11][OH:12])[CH:3]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a stirred solution of 6-bromo-2-methylpyrimidine-4-carbaldehyde (11 g, 54.7 mmol, Preparation #17 step 1) and NH2OH.HCl (7.61 g, 109 mmol, Sisco Research Labs) in ethanol (75 mL) and water (25 mL) was added sodium acetate acetate (13.47 g, 164 mmol). The reaction mixture was heated to reflux at about 90° C. for about 1 h. The mixture was cooled to RT and diluted with water (200 mL). The separated product (solid) was collected by filtration, washed with water and dried under vacuum to afford 6-bromo-2-methylpyrimidine-4-carbaldehyde oxime 4.0 g (33.8%), 1H NMR (400 MHz, DMSO) δ: 12.43 (s, 1H), 8.01 (s, 1H), 7.78 (s, 1H), 2.61 (s, 3H), MS m/z: 216 (negative mode).

Workup

temperatureThe reaction mixture was heated
temperatureThe mixture was cooled to RT
filtrationThe separated product (solid) was collected by filtration
washwashed with water
customdried under vacuum

Sources & evidence

ORD record: ord-9eb1ee3269684dae9f81e4efe5659cd3
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09029409B2

Linked notes

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