Styrene → N-(4-methoxybenzyl)-2-methyl-6-(5-phenyl-4,5-dihydroisoxazol-3-yl)pyrimidine-4-carboxamide

HRID 572648Notes

Reaction equation

HRID 572648 reaction equation
[OH:1][N:2]=[CH:3][C:4]1[N:9]=[C:8]([CH3:10])[N:7]=[C:6]([C:11]([NH:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)=[O:12])[CH:5]=1.[CH2:23]=[CH:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.Cl[O-].[Na+]>C(Cl)Cl.O>[CH3:22][O:21][C:18]1[CH:17]=[CH:16][C:15]([CH2:14][NH:13][C:11]([C:6]2[CH:5]=[C:4]([C:3]3[CH2:23][CH:24]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[O:1][N:2]=3)[N:9]=[C:8]([CH3:10])[N:7]=2)=[O:12])=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 7501StyreneHCID 23665760Sodium HypochloriteHCID 1364132316-((hydroxyimino)methyl)-N-(4-methoxybenzyl)-2-methylpyrimidine-4-carboxamide

Product 1

HCID 71466358N-(4-methoxybenzyl)-2-methyl-6-(5-phenyl-4,5-dihydroisoxazol-3-yl)pyrimidine-4-carboxamideYield 34.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred suspension of 6-((hydroxyimino)methyl)-N-(4-methoxybenzyl)-2-methylpyrimidine-4-carboxamide (0.15 g, 0.50 mmol, Preparation #B.1.1) and styrene (0.057 g, 0.50 mmol) in DCM (10 mL) was added 4% sodium hypochlorite solution (1.5 mL, Sd Fine Chem.) drop wise for about 10 min at RT and stirred for about another 2 h. The reaction mixture was diluted with water (50 mL) and the product extracted with DCM (3×25 mL). The organic layer was dried over sodium sulphate and evaporated to dryness under reduced pressure. The resulting mixture was purified by silica gel (60-120 mesh) chromatography eluting with 20 to 30% of EtOAc in hexane. Relevant fractions containing the target compound were combined and evaporated to dryness under reduced pressure to afford N-(4-methoxybenzyl)-2-methyl-6-(5-phenyl-4,5-dihydroisoxazol-3-yl)pyrimidine-4-carboxamide as a white solid 0.07 g (34%). LC/MS (Table 1, method-b) Rt=1.93 min; MS m/z: 403 (M+H).

Workup

  1. extractionthe product extracted with DCM (3×25 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 gel (60-120 mesh) chromatography
  5. washeluting with 20 to 30% of EtOAc in hexane
  6. additionRelevant fractions containing the target compound
  7. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-bd397ad774234742a66172c4e2623e73
Source dataset
uspto-grants-2015_05
Patent number
US09029409B2

Reaction notes

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