4-Methoxybenzyl alcohol → 7-chloro-5-(4-methoxybenzyloxy)-3-methylpyrido[4,3-d]pyrimidin-4(3H)-one

HRID 1023317Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][OH:8])=[CH:5][CH:4]=1.[H-].[Na+].Cl[C:14]1[C:23]2[C:22](=[O:24])[N:21]([CH3:25])[CH:20]=[N:19][C:18]=2[CH:17]=[C:16]([Cl:26])[N:15]=1>CN(C=O)C>[Cl:26][C:16]1[N:15]=[C:14]([O:8][CH2:7][C:6]2[CH:9]=[CH:10][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[C:23]2[C:22](=[O:24])[N:21]([CH3:25])[CH:20]=[N:19][C:18]=2[CH:17]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 4-methoxybenzylalcohol (596 μL, 4.78 mmol) in anhydrous DMF (20 mL) was added NaH (208 mg, 60% dispersion in mineral oil, 5.20 mmol) at 0° C. The mixture was stirred at 0° C. for 10 minutes before 5,7-dichloro-3-methylpyrido[4,3-d]pyrimidin-4(3H)-one (1.00 g, 4.35 mmol) was slowly added. The resulting mixture was heated at 80° C. overnight, cooled down, quenched with H2O (200 mL), and extracted with EtOAc (3×100 mL). The combined organic layer was dried over MgSO4 and evaporated under reduced pressure to afford crude 7-chloro-5-(4-methoxybenzyloxy)-3-methylpyrido[4,3-d]pyrimidin-4(3H)-one as a yellow solid.

Workup

additionwas slowly added
temperaturecooled down
customquenched with H2O (200 mL)
extractionextracted with EtOAc (3×100 mL)
dry with materialThe combined organic layer was dried over MgSO4
customevaporated under reduced pressure

Sources & evidence

ORD record: ord-06f4dfd477ab494384ecf199e866c74a
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08722692B2

Reaction notes

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