5-(6-Chloro-pyridin-3-yl)-1-(3,3-dimethoxy-propyl)-1H-pyrimidine-2,4-dione → 3-[5-(6-Chloro-pyridin-3-yl)-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-propionaldehyde

HRID 12717Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[CH:6][C:5]([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:4][CH:3]=1>C1COCC1>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([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:4][CH:3]=1

Participants

Conditions

Temperature: 40 °C

Procedure

5-(6-Chloro-pyridin-3-yl)-1-(3,3-dimethoxy-propyl)-1H-pyrimidine-2,4-dione (Prep92, 267 mg, 0.82 mmol) was dissolved in THF (10 ml) and then 1N HClaq (0.82 ml) was added. The solution was stirred at 40° C. for 1.5 hours. TEA (116 μl, 0.83 mmol) was added and the solvent was 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 (0.82 ml) was added
customthe solvent was 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-06092e2182fb448f8c85e017bcd16aec
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07727988B2

Reaction notes

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