5-((6-Methyl-3-pyridyl)methyl)-2-(nitroamino)-1H-pyrimidin-4-one → 2-[2-(N-benzyl-N-pyrid-2-ylamino)ethylamino]-5-(6methylpyrid-3-ylmethyl) pyrimid-4-one

HRID 464353Notes

Reaction equation

HRID 464353 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1)[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[N+](N[C:22]1[NH:27][C:26](=[O:28])[C:25]([CH2:29][C:30]2[CH:31]=[N:32][C:33]([CH3:36])=[CH:34][CH:35]=2)=[CH:24][N:23]=1)([O-])=O>N1C=CC=CC=1>[CH2:5]([N:4]([CH2:3][CH2:2][NH:1][C:22]1[NH:27][C:26](=[O:28])[C:25]([CH2:29][C:30]2[CH:31]=[N:32][C:33]([CH3:36])=[CH:34][CH:35]=2)=[CH:24][N:23]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 30183605-((6-Methyl-3-pyridyl)methyl)-2-(nitroamino)-1H-pyrimidin-4-oneHCID 19831051N-(2-aminoethyl)-N-benzylpyridin-2-amine

Product 1

HCID 541804612-[2-(N-benzyl-N-pyrid-2-ylamino)ethylamino]-5-(6methylpyrid-3-ylmethyl) pyrimid-4-one

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-[N-(2-aminoethyl)-N-benzylamino]pyridine (0.95 g) and 2-nitroamino-5-(6-methylpyrid-3-ylmethyl)pyrimid-4-one (0.91 g) were heated together under reflux in pyridine (10 ml) for 20 hr. After stripping, the residue was triturated with ether and recrystallised from methanol to give 2-[2-(N-benzyl-N-pyrid-2-ylamino)ethylamino]-5-(6methylpyrid-3-ylmethyl) pyrimid-4-one, 1.02 g (68%) mp 178°-82° C.

Workup

  1. customthe residue was triturated with ether
  2. customrecrystallised from methanol

Sources & evidence

ORD record
ord-61c41491efcc46e682be658123255ac0
Source dataset
uspto-grants-1985_10
Patent number
US04547506

Reaction notes

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