1-Methylpiperazine → 2-Chloro-4-(4-methylpiperazin-1-yl)pyrimidine

Temperature

-10 °C

A mixture of 2,4-dichloropyrimidine (0.967 g, 6.49 mmol), 1-methylpiperazine (0.65 g, 6.40 mmol), and ethyldiisopropylamine (2.8 mL, 16.22 mmol) in ethanol (13 mL) was stirred at −10° C. for 2 h and then at r.t. overnight. The mixture was partitioned between H2O/brine (3:1; 100 mL) and chloroform (3×70 mL). The combined organic phases were washed once with brine (50 mL) an dried over MgSO4. Removal of solvent yielded a pale-beige solid, which was washed with ethyl acetate/ultrasound to give the desired product as a colourless powder, which was further washed with Et2O. Additional product was obtained upon fractional crystallization of the washing solution. A total of 0.741 g (3.48 mmol, 54%) of 2-chloro-4-(4-methylpiperazin1-yl)pyrimidine was obtained. LC/ESI-MS: m/z=213 [M(35Cl)+H]+; Rt=0.5 min.

1. customat r.t.
2. customovernight
3. customThe mixture was partitioned between H2O/brine (3:1; 100 mL) and chloroform (3×70 mL)
4. washThe combined organic phases were washed once with brine (50 mL)
5. dry with materialan dried over MgSO4
6. customRemoval of solvent
7. customyielded a pale-beige solid, which
8. washwas washed with ethyl acetate/ultrasound

ORD record

ord-0a7a888992884338845f625d16b2ee58

Source dataset

uspto-grants-2009_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07576090B2