5-((6-Methyl-3-pyridyl)methyl)-2-(nitroamino)-1H-pyrimidin-4-one → HCID 13373479, compound

HRID 358461Notes

Reaction equation

HRID 358461 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[S:6][CH:7]=[C:8]([CH2:10][S:11][CH2:12][CH2:13][NH2:14])[N:9]=1)[CH3:3].[N+](N[C:19]1[NH:24][C:23](=[O:25])[C:22]([CH2:26][C:27]2[CH:28]=[N:29][C:30]([CH3:33])=[CH:31][CH:32]=2)=[CH:21][N:20]=1)([O-])=O>C(O)C>[CH3:3][N:2]([CH2:4][C:5]1[S:6][CH:7]=[C:8]([CH2:10][S:11][CH2:12][CH2:13][NH:14][C:19]2[NH:24][C:23](=[O:25])[C:22]([CH2:26][C:27]3[CH:28]=[N:29][C:30]([CH3:33])=[CH:31][CH:32]=3)=[CH:21][N:20]=2)[N:9]=1)[CH3:1]

Participants

4

Reactant 2

HCID 30183605-((6-Methyl-3-pyridyl)methyl)-2-(nitroamino)-1H-pyrimidin-4-oneHCID 109773182-(Dimethylaminomethyl)-4-(2-aminoethylthiomethyl)thiazole

Product 1

HCID 13373479HCID 13373479, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Following the procedure of Example 1, 0.75 g. of 2-(2-dimethylaminomethyl-4-thiazolylmethylthio)ethylamine and 0.78 g. of 2-nitroamino-5-(6-methyl-3-pyridyl)methyl-4-pyrimidone were dissolved in 5 ml. of anhydrous ethanol and the resulting solution refluxed for about 1 day. The solvents were removed by evaporation and the residue extracted with ethyl acetate. The ethyl acetate extract was washed with water and dried. Evaporation of the ethyl acetate yielded crystals of 2-[2-(2-dimethylaminomethyl-4-thiazolylmethylthio)ethyl]amino-5-(6-methyl-3-pyridyl)methyl-4-pyrimidone which melted at about 154°-5° C. after recrystallization from an ethyl acetate-ether solvent mixture; yield=0.56 g.

Workup

  1. customThe solvents were removed by evaporation
  2. extractionthe residue extracted with ethyl acetate
  3. extractionThe ethyl acetate extract
  4. washwas washed with water
  5. customdried
  6. customEvaporation of the ethyl acetate yielded crystals of 2-[2-(2-dimethylaminomethyl-4-thiazolylmethylthio)ethyl]amino-5-(6-methyl-3-pyridyl)methyl-4-pyrimidone which melted at about 154°-5° C.
  7. customafter recrystallization from an ethyl acetate-ether solvent mixture

Sources & evidence

ORD record
ord-3385722b42c1441da76c2b42811c2528
Source dataset
uspto-grants-1984_08
Patent number
US04468399

Reaction notes

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