2-Nitroamino-5-(4-pyridyl)methyl-4-pyrimidone → 2-[4-(N-propyl-N-pyrid-2-ylamino)butylamino]-5-pyrid-4-ylmethylpyrimid-4-one

HRID 464373Notes

Reaction equation

HRID 464373 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1)[CH2:7][CH2:8][CH3:9].[N+](N[C:20]1[NH:25][C:24](=[O:26])[C:23]([CH2:27][C:28]2[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=2)=[CH:22][N:21]=1)([O-])=O>N1C=CC=CC=1.O>[CH2:7]([N:6]([CH2:5][CH2:4][CH2:3][CH2:2][NH:1][C:20]1[NH:25][C:24](=[O:26])[C:23]([CH2:27][C:28]2[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=2)=[CH:22][N:21]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1)[CH2:8][CH3:9]

Participants

5

Reactant 2

HCID 133734742-Nitroamino-5-(4-pyridyl)methyl-4-pyrimidoneHCID 201866172-[N-(4-aminobutyl)-N-propylamino]pyridine

Product 1

HCID 202628942-[4-(N-propyl-N-pyrid-2-ylamino)butylamino]-5-pyrid-4-ylmethylpyrimid-4-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

2-[N-(4-aminobutyl)-N-propylamino]pyridine (0.9 g) and 2-nitroamino-5-pyrid-4-ylmethylpyrimid-4-one (0.72 g) were heated together under reflux in pyridine (2.5 ml) for 21 hr. After stripping the residue was taken up in water, basified, and extracted with ether. The aqueous was acidified (pH 6.5), extracted with dichloromethane and stripped to give an oil which was crystallized from ethanol/water to give 2-[4-(N-propyl-N-pyrid-2-ylamino)butylamino]-5-pyrid-4-ylmethylpyrimid-4-one 1.2 H2O; 0.45 g (38%) m.p. 58°-60° C.

Workup

  1. extractionextracted with ether
  2. extractionextracted with dichloromethane
  3. customto give an oil which
  4. customwas crystallized from ethanol/water

Sources & evidence

ORD record
ord-f64d459803bd43d99f8bb8ef37d8f4f0
Source dataset
uspto-grants-1985_10
Patent number
US04547506

Reaction notes

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