1-Bromopentadecane → HCID 67356403, compound

HRID 1846189Notes

Reaction equation

HRID 1846189 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][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39].[Li]CCCC>C1COCC1.CCCCC>[CH2:1]([O:8][C:9]1[C:14]([CH2:15][CH2:39][CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH3:25])=[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 123941-BromopentadecaneHCID 67353995HCID 67353995, compoundHCID 178418339Butyllithium

Product 1

HCID 67356403HCID 67356403, 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 630 μL (2.16 mmol) of 1-bromopentadecane in 20 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 a colorless oil: yield 269 mg (24%); silica gel TLC Rf 0.5 (4:1 hexanes-diethyl ether); 1H NMR (CDCl3) δ0.89 (t, 3H, J=7.2 Hz), 1.20-1.30 (m, 26H), 1.75 (quint, 2H, J=7.2 Hz), 2.29 (s, 6H), 2.47 (s, 3H), 2.76 (dd, 2H, J=8.0, 8.0 Hz), 4.89 (s, 2H), 5.85 (s, 2H) and 7.30-7.42 (m, 5H); 13C NMR (CDCl3) δ 14.08, 14.30, 14.30, 19.27, 22.66 27.72, 29.33, 29.40, 29.50, 29.55, 29.63, 29.63, 29.63, 29.67, 29.67, 29.67, 29.67, 31.61, 31.89, 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 518.4113 (M+H)+ (C34H52N3O requires 518.4110).

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-f2859bec6ae6471683e434a2e2e4eee4
Source dataset
uspto-grants-2015_02
Patent number
US08952025B2

Reaction notes

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