3-(Aminomethyl)-5-bromopyridine → 5-Bromo-6-[[(5-bromo-3-pyridinyl)methyl]amino]-2-methyl-4(3H)-pyrimidone

HRID 359679Notes

Reaction equation

[Br:1][C:2]1[C:3]([OH:10])=[N:4][C:5]([CH3:9])=[N:6][C:7]=1Cl.[NH2:11][CH2:12][C:13]1[CH:14]=[C:15]([Br:19])[CH:16]=[N:17][CH:18]=1>COCCOC>[Br:1][C:2]1[C:3](=[O:10])[NH:4][C:5]([CH3:9])=[N:6][C:7]=1[NH:11][CH2:12][C:13]1[CH:18]=[N:17][CH:16]=[C:15]([Br:19])[CH:14]=1

Participants

Conditions

Temperature: 23 °C

Procedure

A stirred mixture of 5-bromo-6-chloro-2-methyl-4-pyrimidinol (4.54 g, 20.3 mmol) and 5-aminomethyl-3-bromopyridine (11.4 g, 61.0 mmol) in 1,2-dimethoxyethane (40 mL) was heated at reflux for 18 hours. The mixture was cooled to 23° C. The precipitate which formed was isolated, rinsed with 1,2-dimethoxyethane and water, and then recrystallized from methanol to provide the title compound as a white, analytically pure product (5.16 g, 13.8 mmol, 68% of theory): mp 241-242 C.; Rf 0.62 (20% MeOH in EtOAc); 1H NMR (DMSO-D6, 400 MHz)δ8.56 (d, J=2 Hz, 1H), 8.49 (d, J=2 Hz, 1H), 7.92 (m, 1H), 7.33 (t, J=6 Hz, 1H), 4.55 (d, J=6 Hz, 2H), 2.16 (s, 3H); IR (KBr) 3400 (NH), 2700-3000 (CH), 1640 (C=O) cm-1 ; UV (MeOH)λ278 (ε12,400); mass spectrum m/e 372 (M+, 54%), 374 (M+, 100%), 376 (M+, 52%), 185 (C6H6BrN2, 78%).

Workup

temperaturewas heated
temperatureat reflux for 18 hours
customThe precipitate which formed
customwas isolated
washrinsed with 1,2-dimethoxyethane and water
customrecrystallized from methanol

Sources & evidence

ORD record: ord-fec2a0b233834bc0bc96b528aeeea75d
Source dataset: uspto-grants-1991_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05002949

Reaction notes

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