Water → HCID 178492101, compound

HRID 1589402Notes

Reaction equation

HRID 1589402 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH2:9][CH2:10][CH2:11][CH2:12][NH:13][C:14]2[NH:15][CH:16]=[CH:17][C:18](=[O:20])[N:19]=2)=[N:5][CH:6]=[CH:7][CH:8]=1.[N:21]1[CH:26]=[CH:25][C:24]([CH:27]=[O:28])=[CH:23][CH:22]=1.C(=O)(O)[O-].[K+].O>Cl>[CH3:1][O:2][C:3]1[C:4]([CH2:9][CH2:10][CH2:11][CH2:12][NH:13][C:14]2[NH:15][CH:16]=[C:17]([CH:27]([C:24]3[CH:25]=[CH:26][N:21]=[CH:22][CH:23]=3)[OH:28])[C:18](=[O:20])[N:19]=2)=[N:5][CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 133894-PyridinecarboxaldehydeHCID 516893Potassium BicarbonateHCID 178492098HCID 178492098, compound

Product 1

HCID 178492101HCID 178492101, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

2-[[4-(3-Methoxy-2-pyridyl)butyl]amino]-4-(1H)-pyrimidinone (0.14 g) and pyridine-4-aldehyde (0.06 g) were refluxed in concentrated hydrochloric acid (1 ml) for 5 hours. The solution was cooled and neutralised by the addition of potassium bicarbonate. Water (2 ml) was added, the aqueous layer was then decanted from the red coloured oil which was washed with more water. The oil was subjected to chromatography on silica gel using gradient elution (100% chloroform→2% Methanol in chloroform). The fractions containing the desired product were collected, combined and evaporated under reduced pressure to afford the title compound as an oil; δ(CDCl3) 1.67 (4H, m), 2.80 (2H, t), 3.36 (2H, m), 3.80 (3H, s), 5.72 (1H, s), 7.07 (2H, d), 7.35 (2H, d), 7.49 (1H, s), 7.87 (1H, t), 8.43 (2H, m) ppm.

Workup

  1. temperatureThe solution was cooled
  2. customthe aqueous layer was then decanted from the red coloured oil which
  3. washwas washed with more water
  4. washThe oil was subjected to chromatography on silica gel using gradient elution (100% chloroform→2% Methanol in chloroform)
  5. additionThe fractions containing the desired product
  6. customwere collected
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-c01609b71c774528952ec79dfcdf5475
Source dataset
uspto-grants-1986_02
Patent number
US04569996

Reaction notes

Loading…