Sodium Nitrite → HCID 57761731, compound

Participants

Reaction Conditions

Reaction Steps

To a cooled solution of 6-{4-[6-(3-chloro-4-fluoro-phenyl)-2-(2-methyl-pyrrolidin-1-yl)-pyrimidin-4-yl]-piperazin-1-yl}-5-methyl-pyridin-3-ylamine (146 mg, 0.303 mmol) in 10% aqueous H2SO4 add NaNO2 (22 mg, 0.318 mmol) in 1 ml of water, dropwise. Stir the solution at 0° C. for 30 minutes. Heat the mixture at 90° C. for 1 hour. Cool to room temperature, adjust the pH to 7, and extract with EtOAc. Wash with brine, dry the solution (Na2SO4), and concentrate under reduced pressure. Purify the residue by flash column chromatography eluting with EtOAc:Hexanes (1:1) to afford 6-{4-[6-(3-chloro-4-fluoro-phenyl)-2-(2-methyl-pyrrolidin-1-yl)-pyrimidin-4-yl]-piperazin-1-yl}-5-methyl-pyridin-3-ol as an off white solid. 1H NMR (300 MHz, CDCl3): δ1.29 (t, 3H, J=6.3 Hz, CH3); 1.69 (m, 1H, CH2CH2); 1.90 (m, 1H, CH2CH2); 2.05 (m, 2H, CH2CH2); 2.29 (s, 3H, Ar—CH3); 3.11 (m, 4H); 3.67 (m, 4H); 3.78 (m, 4H); 4.35 (m, 1H); 6.23 (s, 1H, Ar—H); 7.03 (d, J=2.4 Hz, 1H); 7.16 (m, 1H); 7.72 (d, 1H, J=2.7 Hz); 7.86 (m, 1H); 8.04 (m, 1H).

Provenance & Evidence