4-(5-Bromo-3-methyl-2-pyridinyl)butylamine → HCID 13094282, compound

HRID 1153746Notes

Reaction equation

HRID 1153746 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH3:13])[C:5]([CH2:8][CH2:9][CH2:10][CH2:11][NH2:12])=[N:6][CH:7]=1.[N+](N[C:18]1[NH:23][C:22](=[O:24])[C:21]([CH2:25][C:26]2[CH:27]=[N:28][C:29]([CH3:33])=[CH:30][C:31]=2[CH3:32])=[CH:20][N:19]=1)([O-])=O>C1(OC)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([CH3:13])[C:5]([CH2:8][CH2:9][CH2:10][CH2:11][NH:12][C:18]2[NH:23][C:22](=[O:24])[C:21]([CH2:25][C:26]3[CH:27]=[N:28][C:29]([CH3:33])=[CH:30][C:31]=3[CH3:32])=[CH:20][N:19]=2)=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 130942724-(5-Bromo-3-methyl-2-pyridinyl)butylamineHCID 18470123HCID 18470123, compound

Product 1

HCID 13094282HCID 13094282, compoundYield 60.3%

Reagents, catalysts & solvents 1

HCID 7519AnisoleSolvent

Procedure

A mixture of 5-bromo-2-(4-aminobutyl)-3-methyl pyridine, (0.68 g) and 2-nitroamino-5-(4,6-dimethyl-3-pyridylmethyl)-4-pyrimidone (0.83 g) in anisole (25 ml) were refluxed for 4 hrs. Petroleum ether was added to precipitate the product which was then chromatographed on a silica gel column eluting with chloroform. The product was crystallised from ethyl acetate to give 2-[4-(5-bromo-3-methylpyrid-2-yl)-butylamino]-5-(4,6-dimethyl-3-pyridylmethyl)-4-pyrimidone (0.77 g) m.p. 110°-112° C.

Workup

  1. temperaturewere refluxed for 4 hrs
  2. customto precipitate the product which
  3. customwas then chromatographed on a silica gel column
  4. washeluting with chloroform
  5. customThe product was crystallised from ethyl acetate

Sources & evidence

ORD record
ord-be4d7c09555f4d259e213785ade0f53f
Source dataset
uspto-grants-1984_12
Patent number
US04486434

Reaction notes

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