Benzyl Bromide → HCID 54757317, compound

HRID 1782165Notes

Reaction equation

HRID 1782165 reaction equation
[CH2:1]([C:5]1[NH:6][C:7](=[O:15])[C:8]2[C:13]([CH3:14])=[N:12][S:11][C:9]=2[N:10]=1)[CH:2]([CH3:4])[CH3:3].C([O-])([O-])=O.[K+].[K+].[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CN(C=O)C>[CH2:22]([N:6]1[C:7](=[O:15])[C:8]2[C:13]([CH3:14])=[N:12][S:11][C:9]=2[N:10]=[C:5]1[CH2:1][CH:2]([CH3:4])[CH3:3])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 135979570HCID 135979570, compound

Product 1

HCID 54757317HCID 54757317, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
10 °C

Procedure

To a solution of the 6-isobutyl-3-methyl-5H-isothiazolo[5,4-d]pyrimidin-4-one (method 26) (11 g, 49 mmol) in 60 ml of anhydrous DMF at 0° C., was added 13.8 g (100 mmol) of anhydrous K2CO3 followed by benzyl bromide (9.3 g, 54 mmol) and the mixture was stirred at 0-20° C. overnight. The TLC of the reaction mixture showed the complete disappearance of the SM. The reaction mixture was poured into ice-cold water and extracted with EtOAc (3×100 ml). The combined extracts were washed with water (100 ml), brine (100 ml), dried (Na2SO4) and concentrated. The TLC and the 1H NMR showed the presence of two products N alkylated as well as O-alkylated products in a ratio of 75:25. The products were separated by column (silica gel) chromatography using 10% EtOAc in hexanes. The major N-alkylated product 5-benzyl-6-isobutyl-3-methyl-5H-isothiazolo[5,4-d]pyrimidin-4-one was isolated as white crystalline solid (10.8 g, 70%). 1H NMR (300 MHz) δ 0.94 (d, 6H), 2.23-2.37 (m, 1H), 2.64 (d, 2H), 2.82 (s, 3H), 5.38 (s, 2H), 7.10-7.38 (m, 5H).

Workup

  1. additionThe reaction mixture was poured into ice-cold water
  2. extractionextracted with EtOAc (3×100 ml)
  3. washThe combined extracts were washed with water (100 ml), brine (100 ml)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe products were separated by column (silica gel) chromatography

Sources & evidence

ORD record
ord-e08fb2cf7f6d41a0a3fa572f3e25be05
Source dataset
uspto-grants-2009_03
Patent number
US07498333B2

Reaction notes

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