1-Bromo-3-methylbutane → HCID 23287919, compound

HRID 367268Notes

Reaction equation

HRID 367268 reaction equation
[CH2:1]([N:5]1[C:10](=[O:11])[CH:9]=[C:8]([CH3:12])[NH:7][C:6]1=[O:13])[CH2:2][CH2:3][CH3:4].C([O-])([O-])=O.[K+].[K+].Br[CH2:21][CH2:22][CH:23]([CH3:25])[CH3:24]>CC(C)=O>[CH2:1]([N:5]1[C:10](=[O:11])[CH:9]=[C:8]([CH3:12])[N:7]([CH2:21][CH2:22][CH:23]([CH3:25])[CH3:24])[C:6]1=[O:13])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 78911-Bromo-3-methylbutaneHCID 11430Potassium CarbonateHCID 70528Uracil, 3-butyl-6-methyl-

Product 1

HCID 23287919HCID 23287919, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
23 °C

Procedure

To 5.0 g (27 mmol) of 3-butyl-6-methyluracil in 100 mL of acetone was added 14.9 g (108 mmol) of K2CO3 followed by 4.07 g (27 mmol) of 1-bromo-3-methyl butane. The resulting mixture was refluxed for 48 h. After cooling to 23° C., the reaction mixtyre was filtered and evaporated to give the 8.2 g (24 mmol, a 91% yield) of the title compound as a yellow oil. Yield 91%.; 1H NMR (300 MHz, CDCl3); δ 0.91-0.98 (m, 6H), 1.25 (s, 3H), 1.32-1.40 (m, 2H), 1.48-1.80 (m, 5H), 2.15 (s, 3H), 3.67-3.83 (m, 2H), 3.88-3.96 (m, 2H) 5.57 (s, 1H); IR (KBr, cm31 1): 3476w, 2958w, 2933w, 2872m, 1701s, 1538m, 1432m, 1364m; MS (ES) m/z (relative intensity): 253 (M+ +H).

Workup

  1. temperatureThe resulting mixture was refluxed for 48 h
  2. filtrationthe reaction mixtyre was filtered
  3. customevaporated
  4. customto give the 8.2 g (24 mmol

Sources & evidence

ORD record
ord-fb08c652a4ca424083cb58f556c2563c
Source dataset
uspto-grants-2000_10
Patent number
US06133273

Reaction notes

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