2-(Dimethylaminomethyl)-4-(2-aminoethylthiomethyl)thiazole → HCID 135978008, compound

HRID 358464Notes

Reaction equation

HRID 358464 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][CH:30]=[CH:31][CH:32]=2)=[C:21]([CH3:33])[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][CH:30]=[CH:31][CH:32]=3)=[C:21]([CH3:33])[N:20]=2)[N:9]=1)[CH3:1]

Participants

4

Reactant 2

HCID 109773182-(Dimethylaminomethyl)-4-(2-aminoethylthiomethyl)thiazoleHCID 136203609HCID 136203609, compound

Product 1

HCID 135978008HCID 135978008, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A reaction mixture was prepared from 1.16 g. of 2-[2-dimethylaminomethyl-4-thiazolylmethylthio]ethylamine, 1.31 g. of 2-nitroamino-5-(3-pyridyl)methyl-6-methyl-4-pyrimidone and 25 ml. of anhydrous ethanol. The reaction mixture was heated at reflux temperature for about 5 days after which time the ethanol was removed by evaporation. The residue was chromatographed using high pressure liquid gradient elution chromatography (silica-ethanol/ethyl acetate/ammonium hydroxide). Fractions containing 2-[2-(2-dimethylaminomethyl-4-thiazolylmethylthio)ethyl]amino-5-(3-pyridyl)methyl-6-methyl-4-pyrimidone were combined and the solvents removed from the combined fractions. 1.1 g. of crystalline material was obtained which melted at about 130°-131° C. after recrystallization from a mixture of ethanol and ether; yield=1.03 g. 2-[2-(2-dimethylaminomethyl-4-thiazolylmethylthio)ethyl]amino-5-(3-pyridyl)methyl-6-methyl-4-pyrimidone thus prepared had the following analysis:

Workup

  1. customA reaction mixture was prepared from 1.16 g
  2. temperatureThe reaction mixture was heated
  3. customwas removed by evaporation
  4. customThe residue was chromatographed
  5. washpressure liquid gradient elution chromatography (silica-ethanol/ethyl acetate/ammonium hydroxide)
  6. additionFractions containing 2-[2-(2-dimethylaminomethyl-4-thiazolylmethylthio)ethyl]amino-5-(3-pyridyl)methyl-6-methyl-4-pyrimidone
  7. customthe solvents removed from the combined fractions
  8. customof crystalline material was obtained which melted at about 130°-131° C.
  9. customafter recrystallization
  10. additionfrom a mixture of ethanol and ether
  11. custom2-[2-(2-dimethylaminomethyl-4-thiazolylmethylthio)ethyl]amino-5-(3-pyridyl)methyl-6-methyl-4-pyrimidone thus prepared

Sources & evidence

ORD record
ord-2bad943124f64cd7a94e9802445b0936
Source dataset
uspto-grants-1984_08
Patent number
US04468399

Reaction notes

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