3-({4-[(Piperidin-1-yl)methyl]pyridin-2-yl}oxy)propan-1-amine → 2-[3-[4-(Piperidinomethyl)pyrid-2-yloxy]propylamino]-5-(1-methyl-2-oxopyridin-4-ylmethyl)pyrimidin-4-one
Reaction equation
[N:1]1([CH2:7][C:8]2[CH:13]=[CH:12][N:11]=[C:10]([O:14][CH2:15][CH2:16][CH2:17][NH2:18])[CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[N+](N[C:23]1[NH:28][C:27](=[O:29])[C:26]([CH2:30][C:31]2[CH:36]=[CH:35][N:34]([CH3:37])[C:33](=[O:38])[CH:32]=2)=[CH:25][N:24]=1)([O-])=O>C(O)C>[N:1]1([CH2:7][C:8]2[CH:13]=[CH:12][N:11]=[C:10]([O:14][CH2:15][CH2:16][CH2:17][NH:18][C:23]3[NH:28][C:27](=[O:29])[C:26]([CH2:30][C:31]4[CH:36]=[CH:35][N:34]([CH3:37])[C:33](=[O:38])[CH:32]=4)=[CH:25][N:24]=3)[CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
3-[4-(Piperidinomethyl)pyrid-2-yloxy]propylamine (1.12 g) and 2-nitroamino-5-(1-methyl-2-oxopyridin-4-ylmethyl)pyrimidin-4-one (1.11 g) were refluxed in ethanol (20 ml) for 40 hours. The reaction mixture was evaporated under reduced pressure and the residue was subjected to medium pressure chromatography on silica gel (eluting with 5% methanol/95% chloroform) to afford the title compound. This was dissolved in isopropanol and treated with a solution of maleic acid (0.51 g) in isopropanol to afford material which was recrystallised from isopropanol/methanol to afford 2-[3-[4-(piperidinomethyl)pyrid-2-yloxy]propylamino]-5-(1-methyl-2-oxopyridin-4-ylmethyl)pyrimidin-4-one dimaleate (0.51 g), m.p. 115°-116.5° C.
Workup
- customThe reaction mixture was evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-9135da599374413cabf27c4647418321
- Source dataset
- uspto-grants-1985_09
- Patent number
- US04540699
Reaction notes
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