Benzaldehyde → 5-(hydroxy(phenyl)methyl)-6-(3-isopropylphenoxy)-1-methyl-3-(3-(tetrahydro-2H-pyran-2-yloxy)propyl)pyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione

Participants

Reaction Conditions

Reaction Steps

To a solution of 6-(3-isopropylphenoxy)-1-methyl-3-(3-(tetrahydro-2H-pyran-2-yloxy)propyl)pyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione (220 mg, 0.50 mmol) in THF (10 mL) at −78° C. was added LDA (2.0 M in THF, 1.25 mL, 2.50 mmol) dropwise. The reaction was stirred at −78° C. for 1 h then a solution of benzaldehyde (106 mg, 1.00 mmol) in THF (2 mL) was added dropwise. The reaction was stirred at −78° C. for 1 h, quenched with aq. NH4Cl (10 mL) then diluted with EA (20 mL) and water (20 mL). The organic layer was dried over Na2SO4 and concentrated to give a residue which was purified by chromatography PE/EA (7:1) to give 5-(hydroxy(phenyl)methyl)-6-(3-isopropylphenoxy)-1-methyl-3-(3-(tetrahydro-2H-pyran-2-yloxy)propyl)pyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione (120 mg, 45% yield) as a solid. LCMS: MH+ 560 and TR=1.869 min.

Provenance & Evidence