1-Bromononane → HCID 67329002, compound

HRID 1846198Notes

Reaction equation

HRID 1846198 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[N:6]=[C:5]([N:10]([CH3:12])[CH3:11])[N:4]=1.Br[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].[Li]CCCC>C1COCC1>[CH2:9]([C:7]1[CH:8]=[C:3]([O:2][CH3:1])[N:4]=[C:5]([N:10]([CH3:12])[CH3:11])[N:6]=1)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

5

Reactant 3

HCID 127421-BromononaneHCID 67329637HCID 67329637, compoundHCID 178418339Butyllithium

Product 1

HCID 67329002HCID 67329002, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
23 °C

Procedure

To a stirred solution containing 1.06 g (6.34 mmol) of 4-methoxy-N,N,6-trimethylpyrimidin-2-amine and 1.32 g (6.34 mmol) of 1-bromononane in 20 mL of anhydrous THF were added 5.15 mL (8.34 mmol) of 1.6 M n-BuLi in hexanes. The reaction mixture was stirred at 23° C. for 20 min. The reaction mixture was quenched with saturated aqueous ammonium chloride and poured into 100 mL of water. The compound was extracted with two 80-mL portions of ethyl acetate. The combined organic layer was washed with one 80-mL portion of brine, dried (MgSO4) and concentrated under diminished pressure. The residue was purified by chromatography on a silica gel column (15×5 cm). Elution with 9:1 hexanes-ethyl acetate afforded the expected product as colorless oil: yield 1.22 g (66%); silica gel TLC Rf 0.7 (9:1 hexanes-ethyl acetate); 1H-NMR (CDCl3) δ 0.85 (t, 3H, J=6.8 Hz), 1.28-1.23 (br m, 14H), 1.82 (quint, 2H, J=7.2 Hz), 2.46 (dd, 2H, J=7.6, 7.6 Hz), 3.14 (s, 6H), 3.85 (s, 3H) and 5.77 (s, 1H); 13C NMR (CDCl3) δ 14.09, 22.66, 28.46, 29.31, 29.32, 29.48, 29.54, 29.59, 31.88, 36.78, 37.83, 37.83, 52.75, 93.03, 162.29, 170.25 and 173.93.

Workup

  1. customThe reaction mixture was quenched with saturated aqueous ammonium chloride
  2. additionpoured into 100 mL of water
  3. extractionThe compound was extracted with two 80-mL portions of ethyl acetate
  4. washThe combined organic layer was washed with one 80-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 9:1 hexanes-ethyl acetate

Sources & evidence

ORD record
ord-1f6462e16d2b465aa4563ff8c11e8ee1
Source dataset
uspto-grants-2015_02
Patent number
US08952025B2

Reaction notes

Loading…