Sodium Hydroxide → HCID 178492100, compound

HRID 1589404Notes

Reaction equation

HRID 1589404 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.[CH3:21][C:22]1[CH:27]=[CH:26][C:25]([CH:28]=[O:29])=[CH:24][N:23]=1.[OH-].[Na+]>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:28]([C:25]3[CH:24]=[N:23][C:22]([CH3:21])=[CH:27][CH:26]=3)[OH:29])[C:18](=[O:20])[N:19]=2)=[N:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 101925666-Methyl-3-pyridinecarboxaldehydeHCID 178492098HCID 178492098, compound

Product 1

HCID 178492100HCID 178492100, compoundYield 31.9%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

2-[[4-(3-Methoxy-2-pyridyl)butyl]amino]-4-(1H)-pyrimidinone (1.42 g, 0.005 mol) was dissolved in concentrated hydrochloric acid (10 ml) and 2-methyl-5-formylpyridine (1.35 g, 0.012 mol) was added. The solution was stirred at reflux temperature for 24 hours, cooled, basified with 10N sodium hydroxide to pH 8.5 and the product left to separate as an oil. The aqueous mother liquor was decanted and the oil subjected to medium pressure liquid chromatography (Kieselgel 60, 230-400 mesh) with methanolic ammonia: dichloromethane (10:90) as eluent. The relevant fractions were combined and evaporated under reduced pressure to afford the title compound (0.63 g). Crystallisation from aqueous methanol afforded the title product as a white crystalline solid, m.p. 82° C.; δ(CDCl3) 1.6 (4H, m), 2.5 (3H, s) 2.75 (2H, m), 3.3 (2H, m), 3.8 (3H, s), 5.7 (1H, s), 7.1 (3H, m), 7.4 (1H, s), 7.65 (1H dd), 7.9 (1H, dd), 8.5 (1H, m) ppm.

Workup

  1. temperatureat reflux temperature for 24 hours
  2. temperaturecooled
  3. waitthe product left
  4. customto separate as an oil
  5. customThe aqueous mother liquor was decanted
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-82ce447d27114e3aa94fa8da333aea20
Source dataset
uspto-grants-1986_02
Patent number
US04569996

Reaction notes

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