HCID 11197766, compound → HCID 67355138, compound

HRID 1846143Notes

Reaction equation

HRID 1846143 reaction equation
[CH3:1][C:2]1[N:3]([C:8]2[N:13]=[C:12]([CH3:14])[C:11]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[C:10]([CH3:23])[N:9]=2)[C:4]([CH3:7])=[CH:5][CH:6]=1.[Li]CCCC.Br[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][O:39][CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1>C1COCC1.CCCCC>[CH3:1][C:2]1[N:3]([C:8]2[N:9]=[C:10]([CH3:23])[C:11]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[C:12]([CH2:14][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][O:39][CH2:40][C:41]3[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=3)[N:13]=2)[C:4]([CH3:7])=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 11197766HCID 11197766, compoundHCID 67353995HCID 67353995, compoundHCID 178418339Butyllithium

Product 1

HCID 67355138HCID 67355138, compound

Reagents, catalysts & solvents 2

HCID 8003PentaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a stirred solution at −78° C. containing 500 mg (1.62 mmol) of 2-(2,5-dimethyl-1H-pyrrol-1-yl)-5-benzyloxy-4,6-dimethylpyrimidine (6) in 10 mL of anhydrous THF were added 1.11 mL (1.76 mmol) of a 1.6 M solution of n-BuLi in pentane followed by 509 mg (1.62 mmol) of 9-bromo-1-(benzyloxy)nonane (1). The reaction mixture was stirred under argon atmosphere at −78° C. for 30 min. then the reaction mixture was warmed to room temperature slowly, and the reaction mixture was stirred overnight. The reaction was quenched with saturated aqueous NaHCO3 and the poured into 70 mL of water. The mixture was then extracted with two portions of 70 mL of ethyl acetate. The combined organic solution was then washed with a portion of 100 mL of brine, dried (MgSO4) and then concentrated under diminished pressure. The residue was purified by chromatography on a silica gel column. Elution with hexanes-ethyl acetate 5:1 gave the expected product as light yellow oil: yield 175 mg (20%). 1H-NMR (CDCl3) δ 7.48-7.37 (m, 10H), 5.93 (s, 2H), 4.94 (s, 2H), 4.55 (s, 2H), 3.51 (t, 2H, J=6.8), 2.84 (t, 2H, J=7.6) 2.52 (s, 3H), 2.39 (s, 6H), 1.82 (m, 2H), 1.65 (m, 2H), 1.33 (m, 12H); 13C-NMR (CDCl3) δ 165.16, 161.60, 152.48, 147.71, 138.79, 136.28, 129.16, 128.59, 128.26, 107.99, 75.29, 72.96, 70.70, 31.70, 29.85, 29.62, 29.52, 27.79, 26.27, 22.73, 19.32, 14.37

Workup

  1. temperaturethe reaction mixture was warmed to room temperature slowly
  2. stirringthe reaction mixture was stirred overnight
  3. customThe reaction was quenched with saturated aqueous NaHCO3
  4. additionthe poured into 70 mL of water
  5. extractionThe mixture was then extracted with two portions of 70 mL of ethyl acetate
  6. washThe combined organic solution was then washed with a portion of 100 mL of brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated under diminished pressure
  9. customThe residue was purified by chromatography on a silica gel column
  10. washElution with hexanes-ethyl acetate 5:1

Sources & evidence

ORD record
ord-0f90948421584e88bbabaa450cea1539
Source dataset
uspto-grants-2015_02
Patent number
US08952025B2

Reaction notes

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