Butyl bromide → HCID 67355069, compound

HRID 1846181Notes

Reaction equation

HRID 1846181 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([CH3:23])=[N:11][C:12]([N:16]2[C:20]([CH3:21])=[CH:19][CH:18]=[C:17]2[CH3:22])=[N:13][C:14]=1[CH3:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:25][CH2:26][CH2:27][CH3:28].[Li]CCCC>C1COCC1.CCCCC>[CH2:1]([O:8][C:9]1[C:14]([CH3:15])=[N:13][C:12]([N:16]2[C:20]([CH3:21])=[CH:19][CH:18]=[C:17]2[CH3:22])=[N:11][C:10]=1[CH2:23][CH2:25][CH2:26][CH2:27][CH3:28])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 8002Butyl bromideHCID 67353995HCID 67353995, compoundHCID 178418339Butyllithium

Product 1

HCID 67355069HCID 67355069, compound

Reagents, catalysts & solvents 2

HCID 8003PentaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
23 °C

Procedure

To a stirred solution at −78° C. containing 1.00 g (3.25 mmol) of 5-(Benzyloxy)-2-(2,5-dimethyl-1H-pyrrol-1-yl)-4,6-dimethylpyrimidine and 233 μL (2.16 mmol) of 4-bromobutane in 30 mL of anhydrous THF were added 2.70 mL (4.32 mmol) of a 1.6 M solution of n-BuLi in pentane. The reaction mixture was stirred at 23° C. for 30 min. The reaction was quenched with saturated aqueous ammonium chloride and then poured into 70 mL of water. The mixture was then extracted with two 70-mL portions of diethyl ether. The combined organic layer was then washed with a 100-mL portion of brine, dried (MgSO4) and then concentrated under diminished pressure. The residue was purified by chromatography on a silica gel column (15×5 cm). Elution with 4:1 hexanes-diethyl ether afforded the expected product as a colorless oil: yield 533 mg (69%); silica gel TLC Rf 0.50 (4:1 hexanes-diethyl ether); 1H NMR (CDCl3) δ 0.90 (t, 3H, J=7.2 Hz), 1.34 (m, 2H), 1.77 (m, 2H), 2.33 (s, 6H), 2.49 (s, 3H), 2.79 (dd, 2H, J=7.6, 7.6 Hz), 4.91 (s, 62), 5.88 (s, 2H) and 7.40-7.44 m, 5H); 13C NMR (CDCl3) δ 13.95, 14.34, 19.29, 22.47, 27.41, 31.59, 31.73, 75.72, 107.94, 107.94, 128.01, 128.01, 128.22, 128.72, 129.30, 136.22, 147.38, 147.38, 152.60, 161.62, 161.62 and 165.08; mass spectrum (APCI), m/z 364.2394 (M+H)+ (C23H30N3O requires 364.2389).

Workup

  1. customThe reaction was quenched with saturated aqueous ammonium chloride
  2. additionpoured into 70 mL of water
  3. extractionThe mixture was then extracted with two 70-mL portions of diethyl ether
  4. washThe combined organic layer was then washed with a 100-mL portion of brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated under diminished pressure
  7. customThe residue was purified by chromatography on a silica gel column (15×5 cm)
  8. washElution with 4:1 hexanes-diethyl ether

Sources & evidence

ORD record
ord-7ac65814987840aa98ea92fa9c194772
Source dataset
uspto-grants-2015_02
Patent number
US08952025B2

Reaction notes

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