Reaction #312628

Reaction equation

sodium hydrogencarbonate

7-(4-bromo-2,6-dimethyl-phenyl)-4-chloro-2,6-dimethyl-thieno[3,2-d]pyrimidine

piperidin-4-ylmethanol

N,N-diisopropylethylamine

→

{1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,6-dimethyl-thieno[3,2-d]pyrimidin-4-yl]-piperidin-4-yl}-methanol

Yield 94.2%

Solvents

ethanol

Conditions

Workup

1. 1
   Temperaturewas heated
2. 2
   Temperatureat reflux for 1 day
3. 3
   Extractionextracted with EtOAc
4. 4
   WashThe organic layer washed with brine
5. 5
   Dryingdried over anhydrous sodium sulfate
6. 6
   Filtrationfiltered
7. 7
   ConcentrationThe filtrate was concentrated under reduced pressure
8. 8
   Otherpurified by a silica gel column chromatography (silica gel: Wako Gel (C200), eluent: hexane/EtOAc=3:1)

Procedure

A mixture of 7-(4-bromo-2,6-dimethyl-phenyl)-4-chloro-2,6-dimethyl-thieno[3,2-d]pyrimidine (500 mg), piperidin-4-ylmethanol (226 mg), N,N-diisopropylethylamine (253 mg) in ethanol (1.5 mL) was heated at reflux for 1 day. The reaction mixture was cooled to room temperature, poured into a saturated aqueous sodium hydrogencarbonate, and then extracted with EtOAc. The organic layer washed with brine, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure and purified by a silica gel column chromatography (silica gel: Wako Gel (C200), eluent: hexane/EtOAc=3:1) to obtain {1-[7-(4-bromo-2,6-dimethyl-phenyl)-2,6-dimethyl-thieno[3,2-d]pyrimidin-4-yl]-piperidin-4-yl}-methanol as a white solid (568 mg).

Source