HCID 67329637, compound → HCID 67329285, compound

HRID 1846194Notes

Reaction equation

HRID 1846194 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][CH2:22][O:23][CH2:24][O:25][CH3:26].[Li]CCCC>C1COCC1>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH2:9][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][O:23][CH2:24][O:25][CH3:26])[N:6]=[C:5]([N:10]([CH3:12])[CH3:11])[N:4]=1

Participants

5

Reactant 3

HCID 67329637HCID 67329637, compoundHCID 85780880HCID 85780880, compoundHCID 178418339Butyllithium

Product 1

HCID 67329285HCID 67329285, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
23 °C

Procedure

To a stirred solution containing 933 mg (5.58 mmol) of 4-methoxy-N,N,6-trimethylpyrimidin-2-amine and 1.5 g (5.58 mmol) of 1-Bromo-9-(methoxymethoxy)nonane in 20 mL of anhydrous THF were added 5.23 mL (8.37 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 1.41 g (71%); silica gel TLC Rf 0.45 (9:1 hexanes-ethyl acetate); 1H-NMR (CDCl3) δ 1.24-1.32 (br m, 10H), 1.82 (m, 4H), 2.48 (dd, 2H, J=8.0, 8.0 Hz), 3.14 (s, 6H), 3.33 (s, 3H), 3.48 (t, 2H, J=6.8 Hz), 3.85 (s, 3H), 4.59 (s, 2H) and 5.76 (s, 1H); 13C NMR (CDCl3) δ 26.18, 28.46, 28.66, 29.29, 29.39, 29.45, 29.54, 29.72, 36.77, 37.81, 37.81, 52.74, 55.04, 67.85, 93.03, 96.35, 162.35, 170.25 and 172.03; mass spectrum (APCI+), m/z 354.2766 (M+H) (C19H36N3O3 requires 254.2757).

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-e6e57c6f0bb44492a8d8325407f5fc84
Source dataset
uspto-grants-2015_02
Patent number
US08952025B2

Reaction notes

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