4-(5-Bromo-3-methyl-2-pyridinyl)butylamine → 2-[4-(5-Bromo-3-methylpyrid-2-yl)butylamino]-5-(1-benzyl-2-oxo-pyrid-4-ylmethyl)4-pyrimidone

HRID 485653Notes

Reaction equation

HRID 485653 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:31]=[CH:30][N:29]([CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C:28](=[O:39])[CH:27]=2)=[CH:20][N:19]=1)([O-])=O>N1C=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:31]=[CH:30][N:29]([CH2:32][C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)[C:28](=[O:39])[CH:27]=3)=[CH:20][N:19]=2)=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 130942724-(5-Bromo-3-methyl-2-pyridinyl)butylamineHCID 703539322-Nitroamino-5-(1-benzyl-2-oxo-pyrid-4-ylmethyl)-4-pyrimidone

Product 1

HCID 704488722-[4-(5-Bromo-3-methylpyrid-2-yl)butylamino]-5-(1-benzyl-2-oxo-pyrid-4-ylmethyl)4-pyrimidoneYield 78%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

4-(5-Bromo-3-methylpyrid-2-yl)butylamine (0.71 gm) and 2-nitroamino-5-(1-benzyl-2-oxo-pyrid-4-ylmethyl)-4-pyrimidone (1.0 gm) were refluxed in pyridine (3 ml) for 8 hrs., an extra 0.13 gm of the amine was added and reaction was refluxed for a further 5.5 hrs. The pyridine was removed in vacuo, the residue was re-evaporated with n-propanol (2×40 ml). The residue was dissolved in warm ethanol (10 ml) ether added and on cooling a white solid was obtained which was recrystallised from acetonitrile-water (9:1) to give 2-[4-(5-bromo-3-methylpyrid-2-yl)butylamino]-5-(1-benzyl-2-oxo-pyrid-4-ylmethyl)4-pyrimidone (1.18 gm) m.p. 140°-144° C.

Workup

  1. customreaction
  2. temperaturewas refluxed for a further 5.5 hrs
  3. customThe pyridine was removed in vacuo
  4. customthe residue was re-evaporated with n-propanol (2×40 ml)
  5. dissolutionThe residue was dissolved in warm ethanol (10 ml) ether
  6. additionadded
  7. temperatureon cooling a white solid
  8. customwas obtained which
  9. customwas recrystallised from acetonitrile-water (9:1)

Sources & evidence

ORD record
ord-919a53e7ea3745b4b0250136802049fb
Source dataset
uspto-grants-1985_08
Patent number
US04537890

Reaction notes

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