Reaction #40960

Reaction equation

5-(6-Methyl-pyridin-2-yl)-1H-pyrimidine-2,4-dione hydrochloride

bromo-chloro-butane

K2CO3

5-(6-Methyl-pyridin-2-yl)-1H-pyrimidine-2,4-dione

bromo-chloro-butane

K2CO3

→

title compound

Yield 157.1%

1-(4-Chloro-butyl)-5-(6-methyl-pyridin-2-yl)-1H-pyrimidine-2,4-dione

Yield 157.1%

Solvents

DMF

DMF

Water

Conditions

Workup

1. 1
   workup.STIRRINGthe mixture stirred for 48 hrs at room temperature
2. 2
   OtherA second run of reaction
3. 3
   workup.STIRRINGAfter stirring the reactions at room temperature for 48 hours
4. 4
   workup.ADDITIONthe two mixtures were mixed
5. 5
   Extractionthe mixture was extracted with ethyl acetate
6. 6
   DryingThe organic phase was dried (Na2SO4)
7. 7
   Filtrationfiltered
8. 8
   Otherevaporated
9. 9
   Otherthe crude was purified by flash chromatography with DCM-MeOH—NH4OH (98-2-0.2)

Procedure

5-(6-Methyl-pyridin-2-yl)-1H-pyrimidine-2,4-dione hydrochloride (Prep 50, 50 mg, 0.208 mmol) and K2CO3 (43 mg, 0.312 mmol) were suspended in dry DMF (2 mL) and stirred for 1 h at room temperature. Then a solution of bromo-chloro-butane (71.3 mg, 0.416 mmol) in dry DMF (0.5 mL) was added dropwise and the mixture stirred for 48 hrs at room temperature. A second run of reaction was performed using 5-(6-Methyl-pyridin-2-yl)-1H-pyrimidine-2,4-dione (135 mg, 0.563 mmol), K2CO3 (116 mg, 0.8445 mmol) and bromo-chloro-butane (193 mg, 1.126 mmol). After stirring the reactions at room temperature for 48 hours, the two mixtures were mixed. Water was added and the mixture was extracted with ethyl acetate. The organic phase was dried (Na2SO4), filtered and evaporated; the crude was purified by flash chromatography with DCM-MeOH—NH4OH (98-2-0.2) to give the title compound as a pale yellow solid (96 mg, 43% yield).

Source