Hydrochloric Acid → HCID 68283326, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of a mixture of methyl 3-(4,6-dimethoxypyrimidin-2-yl)propanoate and methyl 3-(4-ethoxy-6-methoxypyrimidin-2-yl)propanoate (1.71 g, 7.56 mmol) in THF (25 mL), DiBAL-H (1 M in THF, 23.0 mL, 23.0 mmol) was added at 0° C. After stirring for 40 min at 0° C., the reaction mixture was allowed to warm to rt, then diluted with DCM and acidified to pH 1 with 2 N aq. HCl-solution (50 mL). The org. layer was separated and the aq. layer was extracted with DCM (2×), then the aq. layer was bascified with aq. NaHCO3-solution and extracted with DCM (2×). The combined org. layers were dried (MgSO4), filtered and the solvent was removed under reduced pressure. Purification by prep. HPLC (basic) yielded 3-(4,6-dimethoxypyrimidin-2-yl)propan-1-ol and 3-(4-ethoxy-6-methoxypyrimidin-2-yl)propan-1-ol as yellow oils. 3-(4,6-dimethoxypyrimidin-2-yl)propan-1-ol: LC-MS conditions B: tR=0.43 min, [M+H]+=199.10. 3-(4-ethoxy-6-methoxypyrimidin-2-yl)propan-1-ol: LC-MS conditions B: tR=0.50 min, [M+H]+=213.13.

Provenance & Evidence