Pyridine → HCID 20186010, compound

HRID 2309193Notes

Reaction equation

HRID 2309193 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]([O:30][CH3:31])=[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]([O:30][CH3:31])=[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 20186014HCID 20186014, compound

Product 1

HCID 20186010HCID 20186010, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

3-[3-(Piperidinomethyl)phenoxy]propylamine (1.64 g) and 2-nitroamino-5-methoxypyrimidin-4-one (1.12 g) were stirred under reflux, for 40 hours, in ethanol (15 ml). The ethanol was replaced by pyridine (15 ml) and the solution stirred under reflux for a further 10 hours to complete the reaction. The reaction mixture was cooled and evaporated under reduced pressure to give a residue. This was partitioned between water (25 ml) and chloroform (25 ml), the aqueous layer being further extracted with chloroform (2×25 ml). The combined chloroform extracts were dried (MgSO4), evaporated under reduced pressure and subjected to medium pressure chromatography using chloroform: methanol (95 : 5) to give the title compound. The fractions containing the title compound were dissolved in isopropanol and treated with maleic acid (0.6 g) in isopropanol to give 2-[3-[3-(piperidinomethyl)phenoxy]propylamino]-5-methoxypyrimidin-4-one maleate (0.96 g), m.p. 148°-149.5° C (recrystallisation from ethanol).

Workup

  1. temperatureunder reflux for a further 10 hours
  2. customthe reaction
  3. temperatureThe reaction mixture was cooled
  4. customevaporated under reduced pressure
  5. customto give a residue
  6. customThis was partitioned between water (25 ml) and chloroform (25 ml)
  7. extractionthe aqueous layer being further extracted with chloroform (2×25 ml)
  8. dry with materialThe combined chloroform extracts were dried (MgSO4)
  9. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-e1e4eafa45bc4f2a8eb14662e80f3cec
Source dataset
uspto-grants-1987_09
Patent number
US04694008

Reaction notes

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