2,4-Dichloro-5-fluoropyrimidine → 2-chloro-4-ethoxy-5-fluoropyrimidine

To a solution of the product from step (a) (10.0 g, 59.9 mmol) in abs. EtOH (40 mL) at 0° C. under nitrogen atmosphere was added 1M NaOEt/EtOH (61 mL, 61 mmol) and the mixture was stirred for 1 hour. Solvent was evaporated in vacuo and the residue partitioned between H2O and Et2O. The aqueous phase was extracted with Et2O and the combined organic phase was washed with brine, dried (Na2SO4) and evaporated (water aspirator pump, 35° C.) to provide the desired product (8.74 g, 83%) as a yellowish solid: mp 30-32° C. (lit. 31-32° C.); 1H NMR (CDCl3): δ1.46 (t, J=7.0 Hz, 3H), 4.53 (quartet, J=7 Hz, 2H), 8.17 (d, J=2.1 Hz, 1H); MS m/z 179 (M+3, 17%), 177 (M+1, 50%), 149 (100%). Anal. Calcd. for C6H6ClFN2O: C, 40.81; H, 3.42; N, 15.86. Found, C, 40.90; H, 3.45; N, 15.81.

1. customSolvent was evaporated in vacuo
2. customthe residue partitioned between H2O and Et2O
3. extractionThe aqueous phase was extracted with Et2O
4. washthe combined organic phase was washed with brine
5. dry with materialdried (Na2SO4)
6. customevaporated (water aspirator pump, 35° C.)

ORD record

ord-a3d0e1e5bff84cc9b809f00bbcde89bb

Source dataset

uspto-grants-2000_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06143748