Water → 5,6-Dimethyl-2-[(pyridin-2-ylmethyl)amino]pyrimidin-4(3H)-one
Reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][NH2:8].[CH3:9][C:10]1[C:11](=[O:19])[NH:12][C:13](SC)=[N:14][C:15]=1[CH3:16].O.C(OCC)C>CS(C)=O>[CH3:9][C:10]1[C:11](=[O:19])[NH:12][C:13]([NH:8][CH2:7][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)=[N:14][C:15]=1[CH3:16]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 150 °C
Procedure
To a stirred solution of (pyridin-2-ylmethyl)amine (5.8 g, 54 mmol) in dimethyl sulfoxide (15 mL) at ambient temperature was added 5,6-dimethyl-2-(methylthio)pyrimidin-4(3H)-one (7 g, 41 mmol, Step A), and the resulting mixture was stirred at 150° C. overnight. Then water (100 mL) was added carefully into the hot reaction mixture. Upon cooling to ambient temperature, diethyl ether (30 mL) was added. The formed precipitate was collected by filtration and dried to afford 7.0 g (74%) of the titled product as a white solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.77 (s, 3H), 2.04 (s, 3H), 4.55 (s, 2H), 6.81 (bs, 1H), 7.23-7.40 (m, 2H), 7.77 (t, J=7.5 Hz, 1H), 8.53 (bs, 1H), 10.84 (bs, 1H).
Workup
- temperatureUpon cooling to ambient temperature
- filtrationThe formed precipitate was collected by filtration
- customdried
Sources & evidence
- ORD record
- ord-9d33811eadca4b1198d04d4b25979839
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09447051B2
Reaction notes
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