Hydrochloric Acid → 5-(3-bromo-phenyl)-2-hydroxy-3-methyl-6-pyridin-4-yl-3H-pyrimidin-4-one

HRID 1795449Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[C:9](=[O:23])[N:10]([CH3:22])[C:11](SC)=[N:12][C:13]=2[C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)[CH:5]=[CH:6][CH:7]=1.[O:24]1CCOCC1.[OH-].[Na+].Cl>O>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[C:9](=[O:23])[N:10]([CH3:22])[C:11]([OH:24])=[N:12][C:13]=2[C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)[CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 85 °C

Procedure

To a 250 mL RBF, was added 5-(3-bromo-phenyl)-3-methyl-2-methylsulfanyl-6-pyridin-4-yl-3H-pyrimidin-4-one (9.2 g, 23.7 mmol), 28 mL dioxane, and 24 mL 5 N NaOH in H2O. The mixture was warmed up to 85° C. and stirred for 15 h. The mixture was cooled down to 0° C. and neutralized with 1 N HCl in H2O until pH 5. White solid was precipitated. After filtration and washed with water, the 5-(3-bromo-phenyl)-2-hydroxy-3-methyl-6-pyridin-4-yl-3H-pyrimidin-4-one was obtained in 5.76 g as white powder. MS (ES+): 358 (M+H)+; (ES−): 356 (M−H).

Workup

customWhite solid was precipitated
filtrationAfter filtration
washwashed with water

Sources & evidence

ORD record: ord-32ca8116d5224edf93cfb9318bfa8e4a
Source dataset: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07026326B2

Reaction notes

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