2-(Dimethylaminomethyl)-4-(2-aminoethylthiomethyl)thiazole → 2-[2-(2-Dimethylaminomethyl-4-thiazolylmethylthio)ethyl]amino-5-(6-methoxy-3-pyridyl)methyl-4-pyrimidone

HRID 358462Notes

Reaction equation

HRID 358462 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]([O:33][CH3:34])=[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]([O:33][CH3:34])=[CH:31][CH:32]=3)=[CH:21][N:20]=2)[N:9]=1)[CH3:1]

Participants

4

Reactant 2

HCID 109773182-(Dimethylaminomethyl)-4-(2-aminoethylthiomethyl)thiazoleHCID 127838322-Nitroamino-5-(6-methoxy-3-pyridylmethyl)-4-pyrimidone

Product 1

HCID 133734802-[2-(2-Dimethylaminomethyl-4-thiazolylmethylthio)ethyl]amino-5-(6-methoxy-3-pyridyl)methyl-4-pyrimidone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Following the procedure of Example 1, 1.29 g. of 2-(2-dimethylaminomethyl-4-thiazolylmethylthio)ethylamine and 1.54 g. of 2-nitroamino-5-(6-methoxy-3-pyridylmethyl)-4-pyrimidone were dissolved in 50 ml. of ethanol and the resulting solution heated at reflux temperature for about 1 week. The solvent was removed by evaporation and the residue purified by gradient elution chromatography (silica-ethanol/ethyl acetate/ammonium hydroxide). Fractions containing the desired pyrimidone were combined and the solvents removed from the combined fractions. The resulting residue was crystallized from ethyl acetate to yield 2-[2-(2-dimethylaminomethyl-4-thiazolylmethylthio)ethyl]amino-5-(6-methoxy-3-pyridyl)methyl-4-pyrimidone melting at 137°-8° C.

Workup

  1. temperatureat reflux temperature for about 1 week
  2. customThe solvent was removed by evaporation
  3. customthe residue purified by gradient elution chromatography (silica-ethanol/ethyl acetate/ammonium hydroxide)
  4. additionFractions containing the desired pyrimidone
  5. customthe solvents removed from the combined fractions
  6. customThe resulting residue was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-a7907036833d4b2abe32e2783b42fe04
Source dataset
uspto-grants-1984_08
Patent number
US04468399

Reaction notes

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