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

HRID 1294682Notes

Reaction equation

HRID 1294682 reaction equation
[OH:1][CH:2]1[CH:7]2[CH2:8][CH2:9][N:4]([CH2:5][CH2:6]2)[CH2:3]1.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:1][CH:2]2[CH:7]3[CH2:8][CH2:9][N:4]([CH2:5][CH2:6]3)[CH2:3]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-Hydroxy quinuclidine (Aldrich, 254 mg, 2 mmol) in tetrahydrofuran (10 ml) was treated with potassium tert-butoxide (Aldrich, 224 mg, 2 mmol) at ambient temperature for 1 hour. The mixture was treated with 2-iodo-5-bromo-pyrimidine (TCl, 568 mg, 2 mmol), stirred at room temperature for 1 hour, treated with water (5 mL), and extracted with chloroform:isopropyl alcohol (10:1) (3×20 mL). The extracts were combined and concentrated. The title compound was purified by chromatography (SiO2, CH2Cl2: MeOH: NH3H2O, 90:10:2, Rf. 0.20) as oil (210 mg, yield, 71%). 1H NMR (MeOH-d4, 300 MHz) δ 1.56–1.68 (m, 1H), 1.70–1.90 (m, 2H), 2.05–2.30 (m, 2H), 2.79–3.06 (m, 5H), 3.40–3.48 (m, 1H), 5.11 (m, 1H), 8.64 (s, 2h) ppm. MS (DCl/NH3) m/z 284 (M+H)+, 286 (M+H)+.

Workup

  1. extractionextracted with chloroform:isopropyl alcohol (10:1) (3×20 mL)
  2. concentrationconcentrated
  3. customThe title compound was purified by chromatography (SiO2, CH2Cl2: MeOH: NH3H2O, 90:10:2, Rf. 0.20) as oil (210 mg, yield, 71%)

Sources & evidence

ORD record
ord-41b6417800a942b18206d36fb2e2f5e5
Source dataset
uspto-grants-2007_07
Patent number
US07241773B2

Reaction notes

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