Benzyl Bromide → 5-Benzyl-3-methyl-6-propyl-5H-isoxazolo[5,4-d]pyrimidin-4-one

HRID 1782138Notes

Reaction equation

HRID 1782138 reaction equation
[CH3:1][C:2]1[C:10]2[C:9](=[O:11])[NH:8][C:7]([CH2:12][CH2:13][CH3:14])=[N:6][C:5]=2[O:4][N:3]=1.[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[CH2:15]([N:8]1[C:9](=[O:11])[C:10]2[C:2]([CH3:1])=[N:3][O:4][C:5]=2[N:6]=[C:7]1[CH2:12][CH2:13][CH3:14])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 1359795693-methyl-6-propyl-5H-isoxazolo[5,4-d]pyrimidin-4-one

Product 1

HCID 222222815-Benzyl-3-methyl-6-propyl-5H-isoxazolo[5,4-d]pyrimidin-4-oneYield 68%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A suspension of 3-methyl-6-propyl-5H-isoxazolo[5,4-d]pyrimidin-4-one (method 17) (1.698 g, 8.8 mmol), benzylbromide (1.5 g, 8.8 mmol), potassium carbonate (2.43 g, 17.6 mmol) in 10 ml DMF was stirred at room temperature overnight. The mixture was diluted with water, extracted with EtOAc (50 ml×3), the combined organic phases were dried, concentrated, purified by flash column chromatography (elute: hexane-EtOAc=5:1). 1.69 g (68%) of the title compound was obtained as white solid. 1H NMR (DMSO-d6): 0.80 (t, 3H), 1.61 (m, 2H), 2.43 (s, 3H), 2.73 (t, 2H), 5.35 (s, 2H), 7.12-7.35 (m, 5H).

Workup

  1. extractionextracted with EtOAc (50 ml×3)
  2. customthe combined organic phases were dried
  3. concentrationconcentrated
  4. custompurified by flash column chromatography (elute: hexane-EtOAc=5:1)

Sources & evidence

ORD record
ord-fdd43cc6aeab4044b0a5cab0f123088d
Source dataset
uspto-grants-2009_03
Patent number
US07498333B2

Reaction notes

Loading…