Reaction #92206

Reaction equation

5-(4-chlorobenzyl)-6-(3-chlorophenyl)-1-((2-(trimethylsilyl)ethoxy)methyl)furo[2,3-d]pyrimidine-2,4(1H,3H)-dione

2-(3-bromopropoxy)tetrahydro-2H-pyran

K2CO3

→

5-(4-chlorobenzyl)-6-(3-chlorophenyl)-3-(3-(tetrahydro-2H-pyran-2-yloxy)propyl)-1-((2-(trimethylsilyl)ethoxy)methyl) furo[2,3-d]pyrimidine-2,4(1H,3H)-dione

Yield 151.6%

Solvents

EA

water

DMF

Conditions

Workup

1. 1
   Temperaturecooled to RT
2. 2
   WashThe organic layer was washed with brine (3 mL)
3. 3
   Dryingdried over Na2SO4
4. 4
   Concentrationconcentrated to a residue which
5. 5
   Otherwas purified by chromatography PE/EA (5:1)

Procedure

To a solution of 5-(4-chlorobenzyl)-6-(3-chlorophenyl)-1-((2-(trimethylsilyl)ethoxy)methyl)furo[2,3-d]pyrimidine-2,4(1H,3H)-dione (25.88 mg, 0.01 mmol) in DMF (3 mL) was added 2-(3-bromopropoxy)tetrahydro-2H-pyran (11.2 mg, 0.05 mmol) and K2CO3 (6.9 mg, 0.05 mmol). The reaction was stirred at 60° C. for 2 h, cooled to RT, then was diluted with EA (12 mL) and water (4 mL). The organic layer was washed with brine (3 mL), dried over Na2SO4, and concentrated to a residue which was purified by chromatography PE/EA (5:1) to give 5-(4-chlorobenzyl)-6-(3-chlorophenyl)-3-(3-(tetrahydro-2H-pyran-2-yloxy)propyl)-1-((2-(trimethylsilyl)ethoxy)methyl) furo[2,3-d]pyrimidine-2,4(1H,3H)-dione (10 mg, 30.7% yield) as an oil. LCMS: (M++Na) 681 and TR=2.289 min.

Source