Reaction equation
Cl.Cl[CH2:3][C:4]1[C:5]([NH2:11])=[N:6][C:7]([CH3:10])=[N:8][CH:9]=1.C(N(CC)CC)C.[CH3:19][O:20][C:21]1[CH:22]=[C:23]2[C:28](=[CH:29][CH:30]=1)[CH2:27][NH:26][CH2:25][CH2:24]2>CN(C)C=O>[CH3:19][O:20][C:21]1[CH:22]=[C:23]2[C:28](=[CH:29][CH:30]=1)[CH2:27][N:26]([CH2:3][C:4]1[C:5]([NH2:11])=[N:6][C:7]([CH3:10])=[N:8][CH:9]=1)[CH2:25][CH2:24]2Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A suspension of 0.80 g (0.00412 mol) of 5-chloromethyl-2-methyl-pyrimidin-4-ylamine hydrochloride in 17 ml of dimethylformamide was treated with 1.7 ml (0.0124 mol) of triethylamine and 0.87 g (0.0053 mol) of 6-methoxy-1,2,3,4-tetrahydro-isoquinoline and the mixture was stirred at room temperature under argon for 3 hours. The mixture was completely freed from the solvents and the residue was triturated in 20 ml of water. The resulting crystals were filtered off under suction, chromatographed over silica gel with dichloromethane/methanol 9:1 as the eluent and recrystallized from ethyl acetate/n-hexane. 0.26 g (22%) of 5-(6-methoxy-3,4-dihydro-1H-isoquinolin-2-ylmethyl)-2-methyl-pyrimidin-4-ylamine was obtained as white crystals; m.p. 142°-143°.
Workup
- customthe residue was triturated in 20 ml of water
- filtrationThe resulting crystals were filtered off under suction
- customchromatographed over silica gel with dichloromethane/methanol 9:1 as the eluent
- customrecrystallized from ethyl acetate/n-hexane
Sources & evidence
- ORD record
- ord-49d977aebe9445428ad63540d468cc9e
- Source dataset
- uspto-grants-1997_11
- Patent number
- US05688798
Linked notes
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