5-(5,6-Dimethyl-3-pyridylmethyl)-2-nitroamino4-pyrimidone → HCID 13094283, compound

HRID 1153747Notes

Reaction equation

HRID 1153747 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])=[C:30]([CH3:32])[CH:31]=2)=[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])=[C:30]([CH3:32])[CH:31]=3)=[CH:20][N:19]=2)=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 127838315-(5,6-Dimethyl-3-pyridylmethyl)-2-nitroamino4-pyrimidoneHCID 130942724-(5-Bromo-3-methyl-2-pyridinyl)butylamine

Product 1

HCID 13094283HCID 13094283, compoundYield 47%

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-(5,6-dimethyl-3-pyridylmethyl)-4-pyrimidone (0.83 g) in anisole (25 ml) were refluxed for 4 hrs. Excess petroleum ether was added to precipitate the product which was then chromatographed on a silica gel column in CHCl3. The product crystallised under ether to give 2-[4-(5-bromo-3-methyl-pyrid-2-yl)-butylamino]-5-(5,6-dimethyl-3-pyridylmethyl)-4-pyrimidone (0.6 g) m.p. 126°14 8° C.

Workup

  1. temperaturewere refluxed for 4 hrs
  2. customto precipitate the product which
  3. customwas then chromatographed on a silica gel column in CHCl3
  4. customThe product crystallised under ether

Sources & evidence

ORD record
ord-9b86fe856f1c4eb18e353a8305d7c7fe
Source dataset
uspto-grants-1984_12
Patent number
US04486434

Reaction notes

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