1-Bromononane → HCID 67356396, compound

HRID 1846185Notes

Reaction equation

HRID 1846185 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][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33].[Li]CCCC>C1COCC1.CCCCC>[CH2:1]([O:8][C:9]1[C:14]([CH2:15][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])=[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[CH3:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 127421-BromononaneHCID 67353995HCID 67353995, compoundHCID 178418339Butyllithium

Product 1

HCID 67356396HCID 67356396, 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 415 mg (2.16 mmol) of 1-bromononane in 30 mL of anhydrous THF were added 2.70 mL (4.32 mmol) of a 1.60 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 light colorless oil: yield 502 mg (53%); silica gel TLC Rf 0.60 (4:1 hexanes-diethyl ether); 1H NMR (CDCl3) δ0.89 (t, 3H, J=7.2 Hz), 1.20-1.30 (m, 14H), 1.75 (m, 2H), 2.31 (s, 6H), 2.48 (s, 3H), 2.77 (dd, 2H, J=7.6, 7.6 Hz), 4.90 (s, 2H), 5.86 (s, 2H) and 7.40-7.44 (m, 5H); 13C NMR (CDCl3) δ 14.10, 14.33, 19.28, 22.67 27.74, 29.29, 29.29, 29.41, 29.51, 29.57, 31.62, 31.88, 75.72, 107.91, 128.01, 128.22, 128.72, 129.30, 129.30, 136.22, 147.35, 147.35, 152.59, 161.59 and 165.09; mass spectrum (APCI), m/z 434.3172 (M+H)+ (C28H40N30 requires 434.3171).

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-fd6e712789764593ac13b1db64d706fd
Source dataset
uspto-grants-2015_02
Patent number
US08952025B2

Reaction notes

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