5-((6-Methyl-3-pyridyl)methyl)-2-(nitroamino)-1H-pyrimidin-4-one → 2-[4-(5-Bromo-3-aminopyrid-2-yl)butylamino]-5-(6-methylpyrid-3-ylmethyl) 4-pyrimidone

HRID 978365

Reaction equation

HRID 978365 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH2:13])[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]([CH3:32])=[CH:30][CH:31]=2)=[CH:20][N:19]=1)([O-])=O>N1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([NH2:13])[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]([CH3:32])=[CH:30][CH:31]=3)=[CH:20][N:19]=2)=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 30183605-((6-Methyl-3-pyridyl)methyl)-2-(nitroamino)-1H-pyrimidin-4-oneHCID 145374593-Amino-5-bromo-(4-aminobutyl)pyridine

Product 1

HCID 202029052-[4-(5-Bromo-3-aminopyrid-2-yl)butylamino]-5-(6-methylpyrid-3-ylmethyl) 4-pyrimidoneYield 57.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

5-Bromo-2-(4-aminobutyl)-3-aminopyridine (0.5 g) and 2-nitroamino-5-(6-methylpyrid-3-ylmethyl)-4-pyrimidone (0.59 g) were refluxed in pyridine (2 ml) under nitrogen for 9 hours. The pyridine was removed in vacuo and the residual pyridine removed by azeotroping with n-propanol. After chromatography on silica in ethylacetate/ethanol/0.880 ammonia (15:10:2), the residue was crystallised from ethanol-ether and water (2 drops) to give 2-[4-(5-bromo-3-aminopyrid-2-yl)butylamino]-5-(6-methylpyrid-3-ylmethyl) 4-pyrimidone (0.52 g), m.p. 196°-197° C.

Workup

  1. customThe pyridine was removed in vacuo
  2. customthe residual pyridine removed
  3. customby azeotroping with n-propanol
  4. customAfter chromatography on silica in ethylacetate/ethanol/0.880 ammonia (15:10:2), the residue was crystallised from ethanol-ether and water (2 drops)

Sources & evidence

ORD record
ord-4cc55fc972b741b4b8bdd364fd1661fa
Source dataset
uspto-grants-1987_05
Patent number
US04665078

Linked notes

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