Hydrochloric Acid → HCID 86715501, compound

HRID 2284591Notes

Reaction equation

Cl.[F:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:14]([C:15]3[CH:20]=[CH:19][N:18]=[C:17]([O:21]C)[N:16]=3)=[CH:13][CH:12]=[CH:11][N:10]=2)=[CH:5][C:4]=1[CH3:23]>CO>[F:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:14]([C:15]3[NH:16][C:17](=[O:21])[N:18]=[CH:19][CH:20]=3)=[CH:13][CH:12]=[CH:11][N:10]=2)=[CH:5][C:4]=1[CH3:23]

Participants

Conditions

Temperature: 90 °C

Procedure

Aqueous HCl (2N, 20 mL) was added to the stirring solution of 4-(2-(4-fluoro-3-methylphenyl)pyridin-3-yl)-2-methoxypyrimidine (1.3 g) in MeOH (10 mL) and heated at 90° C. for 12 h. The reaction mixture was concentrated by rotary evaporator under reduced pressure and neutralized the resultant pale yellow viscous material with aq. NaHCO3 solution. The slurry thus formed upon neutralization was stirred at room temperature for 20 min. The solid was collected by filtration, washed with water, suction dried. After 6 h, the solid was further dried over P2O5 under high vacuum to provide 6-(2-(4-fluoro-3-methylphenyl)pyridin-3-yl)pyrimidin-2(1H)-one as a white solid (0.87 g). 1H NMR (300 MHz, DMSO-d6): δ 11.92 (s, 1H), 8.74 (dd, J=4.8, 1.7 Hz, 1H), 7.98 (dd, J=7.8, 1.7 Hz, 1H), 7.80 (app d, J=6.0 Hz, 1H), 7.51 (dd, J=7.8, 4.8 Hz, 1H), 7.43 (dd, J=7.7, 2.1 Hz, 1H), 7.24-7.02 (m, 2H), 5.96 (d, J=6.0 Hz, 1H), 2.22 (app s, 3H). 19F NMR (282 MHz, DMSO-d6) δ −117.63.

Workup

concentrationThe reaction mixture was concentrated by rotary evaporator under reduced pressure
customThe slurry thus formed upon neutralization
filtrationThe solid was collected by filtration
washwashed with water, suction
customdried
waitAfter 6 h
dry with materialthe solid was further dried over P2O5 under high vacuum

Sources & evidence

ORD record: ord-c8a09aca46854682aa3c6904a8b0dc61
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09145433B2

Reaction notes

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