Phosphorus oxychloride → 5-(3-Bromo-phenyl)-2-chloro-3-methyl-6-pyridin-4-yl-3H-pyrimidin-4-one

HRID 1795450Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[C:9](=[O:22])[N:10]([CH3:21])[C:11](O)=[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=P(Cl)(Cl)[Cl:25].C([O-])(O)=O.[Na+]>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[C:9](=[O:22])[N:10]([CH3:21])[C:11]([Cl:25])=[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)-2-hydroxy-3-methyl-6-pyridin-4-yl-3H-pyrimidin-4-one (5.76 g, 16.1 mmol), 50 mL POCl3. The mixture was warmed up to 85° C. and stirred for 15 h under nitrogen. The mixture was cooled down to rt and vacuumed down all volatile composites. The black cake obtained was dissolved in dichloromethane, neutralized with sat. NaHCO3. After purified by flash chromatography, the 5-(3-Bromo-phenyl)-2-chloro-3-methyl-6-pyridin-4-yl-3H-pyrimidin-4-one was obtained in 4.72 g as white powder. MS (ES+): 376 (M+H)+; (ES−): 374 (M−H).

Workup

temperatureThe mixture was cooled down to rt
customThe black cake obtained
customAfter purified by flash chromatography

Sources & evidence

ORD record: ord-271920d04eb14f02b0b5df2e8d91ff26
Source dataset: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07026326B2

Reaction notes

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