2,4-Dichloropyrimidine → 2-Chloro-4-ethoxypyrimidine

To a solution of 2,4-dichloropyrimidine (Aldrich, 10.0 g, 67.12 mmol) in abs. EtOH (120 mL) at -3° C. under nitrogen atmosphere was slowly added (over 2 hours) 1M NaOEt/EtOH (68 mL, 68 mmol) and the resulting mixture 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.). The resulting residue was filtered and washed with petroleum ether to provide the desired product (8.05 g, 75%) as a yellowish solid: mp 30-31° C. (lit. 35° C.); 1H NMR (CDCl3): δ1.40 (t, J=7.2 Hz, 3H), 4.44 (quartet, J=7.2 Hz, 2H), 6.62 (d, J=5.7 Hz, 1H), 8.27 (d, J=5.7 Hz, 1H); MS m/z 161 (M+3, 34%), 159 (M+1, 100%). Anal. Calcd. for C6H7ClN2O: C, 45.44; H, 4.45; N, 17.66; Cl, 22.36. Found: C, 45.32; H, 4.41; N, 17.60; Cl, 22.43.

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.)
7. filtrationThe resulting residue was filtered
8. washwashed with petroleum ether

ORD record

ord-d892742794a74671943b186f5508c796

Source dataset

uspto-grants-2000_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06143748