5-(2-Chloro-pyridin-3-yl)-1-(3,3-dimethoxy-propyl)-1H-pyrimidine-2,4-dione → 3-[5-(2-Chloro-pyridin-3-yl)-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-propionaldehyde

HRID 12721Notes

Reaction equation

[Cl:1][C:2]1[C:7]([C:8]2[C:9](=[O:22])[NH:10][C:11](=[O:21])[N:12]([CH2:14][CH2:15][CH:16](OC)[O:17]C)[CH:13]=2)=[CH:6][CH:5]=[CH:4][N:3]=1>C1COCC1>[Cl:1][C:2]1[C:7]([C:8]2[C:9](=[O:22])[NH:10][C:11](=[O:21])[N:12]([CH2:14][CH2:15][CH:16]=[O:17])[CH:13]=2)=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

Conditions

Temperature: 40 °C

Procedure

5-(2-Chloro-pyridin-3-yl)-1-(3,3-dimethoxy-propyl)-1H-pyrimidine-2,4-dione (Prep96, 150 mg, 0.46 mmol) was dissolved in THF (5.6 ml) and 1N HClaq (0.46 ml) was added. The solution was then stirred at 40° C. for 1.5 hours. TEA (0.067 ml, 0.48 mmol) was added and the solvent was carefully removed in vacuum at room temperature. Residue was freeze dried to give a white powder that was used in the next step without further purification (quantitative yield).

Workup

addition1N HClaq (0.46 ml) was added
customthe solvent was carefully removed in vacuum at room temperature
customdried
customto give a white powder that
customwas used in the next step without further purification (quantitative yield)

Sources & evidence

ORD record: ord-815b1655803a4afb9cc70222cbb50008
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07727988B2

Reaction notes

Loading…