2-(Dimethylaminomethyl)-4-(2-aminoethylthiomethyl)thiazole → 2-[2-(2-Dimethylaminomethyl-4-thiazolylmethylthio)ethyl]amino-5-(2-methoxy-4-pyridyl)methyl-4-pyrimidone

HRID 358463Notes

Reaction equation

HRID 358463 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:32]=[CH:31][N:30]=[C:29]([O:33][CH3:34])[CH:28]=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:32]=[CH:31][N:30]=[C:29]([O:33][CH3:34])[CH:28]=3)=[CH:21][N:20]=2)[N:9]=1)[CH3:1]

Participants

4

Reactant 2

HCID 109773182-(Dimethylaminomethyl)-4-(2-aminoethylthiomethyl)thiazoleHCID 127838332-Nitroamino-5-(2-methoxy-4-pyridyl)methyl-4-pyrimidone

Product 1

HCID 133734842-[2-(2-Dimethylaminomethyl-4-thiazolylmethylthio)ethyl]amino-5-(2-methoxy-4-pyridyl)methyl-4-pyrimidone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Following the procedure of Example 1, a reaction mixture was prepared from 1.62 g. of 2-(2-dimethylaminomethyl-4-thiazolylmethylthio)ethylamine and 1.94 g. of 2-nitroamino-5-(2-methoxy-4-pyridyl)methyl-4-pyrimidone and 30 ml. of ethanol. The reaction mixture was stirred and heated at refluxing temperature for about 42 hours. The volatile constituents were removed by evaporation and the residue purified by high pressure liquid gradient elution chromatography (silica-ethanol/ethyl acetate/ammonium hydroxide). Fractions containing 2-[2-(2-dimethylaminomethyl-4-thiazolylmethylthio)ethyl]amino-5-(2-methoxy-4-pyridyl)methyl-4-pyrimidone were combined and the solvent removed therefrom. Recrystallization of the resulting residue from a cyclohexane-ether solvent mixture gave 2-[2-(2-dimethylaminomethyl-4-thiazolylmethylthio)ethyl]amino-5-(2-methoxy-4-pyridyl)methyl-4-pyrimidone melting at 79°-80° C.

Workup

  1. customa reaction mixture was prepared from 1.62 g
  2. temperatureheated
  3. temperatureat refluxing temperature for about 42 hours
  4. customThe volatile constituents were removed by evaporation
  5. customthe residue purified by high pressure liquid gradient elution chromatography (silica-ethanol/ethyl acetate/ammonium hydroxide)
  6. additionFractions containing 2-[2-(2-dimethylaminomethyl-4-thiazolylmethylthio)ethyl]amino-5-(2-methoxy-4-pyridyl)methyl-4-pyrimidone
  7. customthe solvent removed
  8. customRecrystallization of the resulting residue from a cyclohexane-ether solvent mixture

Sources & evidence

ORD record
ord-c8b794a2a1ca458192f36efe16859480
Source dataset
uspto-grants-1984_08
Patent number
US04468399

Reaction notes

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