Pyridine → 2-[3-[3-(Piperidinomethyl)phenoxy]propylamino]-5-(1-methyl-2-oxopyridin-4-ylmethyl)pyrimidin-4-one

HRID 1719554Notes

Reaction equation

HRID 1719554 reaction equation
[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([CH:16]=[CH:17][CH:18]=2)[O:11][CH2:12][CH2:13][CH2:14][NH2:15])[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.N1C=CC=CC=1>C(O)C>[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([CH:16]=[CH:17][CH:18]=2)[O:11][CH2:12][CH2:13][CH2:14][NH:15][C:23]2[NH:28][C:27](=[O:29])[C:26]([CH2:30][C:31]3[CH:36]=[CH:35][N:34]([CH3:37])[C:33](=[O:38])[CH:32]=3)=[CH:25][N:24]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 102205613-(3-(Piperidin-1-ylmethyl)phenoxy)propan-1-amineHCID 70354123HCID 70354123, compound

Product 1

HCID 703539022-[3-[3-(Piperidinomethyl)phenoxy]propylamino]-5-(1-methyl-2-oxopyridin-4-ylmethyl)pyrimidin-4-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

3-[3-(Piperidinomethyl)phenoxy]propylamine (1.12 g) and 2-nitroamino-5-(1-methyl-2-oxopyridin-4-ylmethyl)pyrimidin-4-one (1.11 g) were refluxed in ethanol (8 ml) for 20 hours. As the reaction was incomplete the ethanol was replaced by pyridine (8 ml) and the solution refluxed for a further 6 hours. The reaction mixture was evaporated under reduced pressure and the residue was subjected to medium pressure chromatography on silica gel (eluting with 10% methanol/90% chloroform) to afford the title compound. This was treated with dilute ethanolic HCl to afford material which was recrystallised from isopropanol/ether to afford 2-[3-[3-(piperidinomethyl)phenoxy]propylamino]-5-(1-methyl-2-oxopyridin-4-ylmethyl)pyrimidin-4-one dihydrochloride (0.85 g), m.p. 164°-167° C.

Workup

  1. temperaturethe solution refluxed for a further 6 hours
  2. customThe reaction mixture was evaporated under reduced pressure

Sources & evidence

ORD record
ord-ad5cac794f77405aaff3e7c20a0c73c7
Source dataset
uspto-grants-1985_09
Patent number
US04540699

Reaction notes

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