Styrene → 3-(6-Bromo-2-methylpyrimidin-4-yl)-5-phenyl-4,5-dihydroisoxazole

HRID 572678Notes

Reaction equation

HRID 572678 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([CH3:8])[N:5]=[C:4]([CH:9]=[N:10][OH:11])[CH:3]=1.[CH2:12]=[CH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.Cl[O-].[Na+]>C(Cl)Cl>[Br:1][C:2]1[N:7]=[C:6]([CH3:8])[N:5]=[C:4]([C:9]2[CH2:12][CH:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[O:11][N:10]=2)[CH:3]=1

Participants

5

Reactant 3

HCID 7501StyreneHCID 23665760Sodium HypochloriteHCID 1364132336-Bromo-2-methylpyrimidine-4-carbaldehyde oxime

Product 1

HCID 866759313-(6-Bromo-2-methylpyrimidin-4-yl)-5-phenyl-4,5-dihydroisoxazoleYield 42.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a cold solution of 6-bromo-2-methylpyrimidine-4-carbaldehyde oxime (0.4 g, 1.852 mmol Preparation #17) and styrene (0.257 mL, 2.222 mmol) in DCM (10 mL) was added sodium hypochlorite solution (0.229 mL, 3.70 mmol). The reaction mixture was stirred for about 2 h and diluted with DCM (50 mL), successively washed with water (2×30 mL) and brine (1×30 mL). The organic layer was dried over sodium sulphate and evaporated to dryness under reduced pressure. The resulting mixture was purified by silica gelchromatography eluting with 40% EtOAc in hexane. Relevant fractions containing the required compound were combined and evaporated to dryness under reduced pressure to afford 3-(6-bromo-2-methylpyrimidin-4-yl)-5-phenyl-4,5-dihydroisoxazol 0.25 g (42.4%), 1H NMR (400 MHz, DMSO): δ 8.00 (s, 1H), 7.40 (m, 5H), 5.90 (m, 1H), 3.93 (m, 1H), 3.41 (m, 1H), 2.64 (s, 3H), MS m/z: 320 (M+H)+.

Workup

  1. washsuccessively washed with water (2×30 mL) and brine (1×30 mL)
  2. dry with materialThe organic layer was dried over sodium sulphate
  3. customevaporated to dryness under reduced pressure
  4. customThe resulting mixture was purified by silica gelchromatography
  5. washeluting with 40% EtOAc in hexane
  6. additionRelevant fractions containing the required compound
  7. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-5024bbe0fb7a4553bd5a25f5fe948900
Source dataset
uspto-grants-2015_05
Patent number
US09029409B2

Reaction notes

Loading…