Methyltriphenylphosphonium chloride → HCID 178435233, compound

To a stirred suspension of methyl triphenylphosphonium chloride (1.07 g, 3.0 mmol) in THF (20 ml) at 0° C. was added n-BuLi (1.4 M in hexane, 2.14 ml, 3.0 mmol). The resulting reddish-brown mixture was stirred at this temperature for 0.5 h and then at rt for 0.5 h. A solution of 4-(2,6-dioxo-1,3-dipropyl-2,3,6,9-tetrahydro-1H-purin-8-yl)-bicyclo[2.2.2]octane-1-carbaldehyde (372 mg, 1.0 mmol) in THF (10 ml) was added over a period of 20 minutes and the resulting mixture was stirred overnight (12 h). The reaction mixture was partitioned between saturated aqueous NH2Cl2 (20 ml) and EtOAc (20 ml) and the aqueous phase was extracted with EtOAc (20 ml). The combined organic extracts were washed with saturated aqeuous NaCl (50 ml), dried (MgSO4), filtered and evaporated in vacuo to afford an oil that was purified by radial chromatography (2 mm plate) using a gradient of 0-5% MeOH in CH2Cl2 as eluent. Product-containing fractions were combined and concentrated to afford 140 mg (38%) of a white solid. MS: 371 (MH+).

1. waitat rt for 0.5 h
2. stirringthe resulting mixture was stirred overnight (12 h)
3. customThe reaction mixture was partitioned between saturated aqueous NH2Cl2 (20 ml) and EtOAc (20 ml)
4. extractionthe aqueous phase was extracted with EtOAc (20 ml)
5. washThe combined organic extracts were washed with saturated aqeuous NaCl (50 ml)
6. dry with materialdried (MgSO4)
7. filtrationfiltered
8. customevaporated in vacuo
9. customto afford an oil that
10. customwas purified by radial chromatography (2 mm plate)
11. concentrationconcentrated

ORD record

ord-2e1c59752f48484b9d2eb90a785e6de1

Source dataset

uspto-grants-2009_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07579354B2