Water → 3-((5-Bromopyrimidin-2-yl)oxy)quinuclidine

HRID 969992Notes

Reaction equation

HRID 969992 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]([OH:9])[CH2:2]2.CC(C)([O-])C.[K+].I[C:17]1[N:22]=[CH:21][C:20]([Br:23])=[CH:19][N:18]=1.O>O1CCCC1>[Br:23][C:20]1[CH:19]=[N:18][C:17]([O:9][CH:3]2[CH:4]3[CH2:7][CH2:8][N:1]([CH2:6][CH2:5]3)[CH2:2]2)=[N:22][CH:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 15381(+-)-3-QuinuclidinolHCID 70066515-Bromo-2-iodopyrimidineHCID 23665647Potassium tert-butoxide

Product 1

HCID 210726093-((5-Bromopyrimidin-2-yl)oxy)quinuclidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Quinuclidinol (Aldrich, 254 mg, 2 mmol) in tetrahydrofuran (Aldrich, anhydrous, 10 mL) was treated with potassium tert-butoxide (224 mg, 2 mmol) at ambient temperature for 1 hour. 2-Iodo-5-bromo-pyrimidine (Aldrich, 568 mg, 2 mmol) was then added. After stirring for 30 minutes, the mixture was treated with water (5 mL) and extracted with CHCl3:isopropyl alcohol (10:1, 3×10 mL). The extracts were combined and concentrated under reduced pressure. The title compound was purified by flash chromatography (SiO2, CH2Cl2:MeOH:NH3.H2O, 90:10:1, Rf. 0.15) as a solid (287 mg, yield, 50%). 1H NMR (300 MHz, MeOH-d4) δ 1.52-1.65 (m, 1H), 1.66-1.93 (m, 2H), 2.00-2.15 (m, 1H), 2.22-2.31 (m, 1H), 2.79-3.09 (m, 5H), 3.38-3.49 (m, 1H), 5.06-5.15 (m, 1H), 8.64 (s, 2H) ppm. MS (DCl/NH3) m/z 284 (M+H)+ 286 (M+H)+.

Workup

  1. extractionextracted with CHCl3:isopropyl alcohol (10:1, 3×10 mL)
  2. concentrationconcentrated under reduced pressure
  3. customThe title compound was purified by flash chromatography (SiO2, CH2Cl2:MeOH:NH3.H2O, 90:10:1, Rf. 0.15) as a solid (287 mg, yield, 50%)

Sources & evidence

ORD record
ord-c772819811f148cc85971e8064de11dc
Source dataset
uspto-grants-2007_12
Patent number
US07309699B2

Reaction notes

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