2-(Dimethylaminomethyl)-4-(2-aminoethylthiomethyl)thiazole → HCID 13373508, compound

HRID 358468Notes

Reaction equation

HRID 358468 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].CS[C:17]1[NH:22][C:21](=[S:23])[C:20]([CH2:24][C:25]2[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=2)=[CH:19][N:18]=1>N1C=CC=CC=1>[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:17]2[NH:22][C:21](=[S:23])[C:20]([CH2:24][C:25]3[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=3)=[CH:19][N:18]=2)[N:9]=1)[CH3:1]

Participants

4

Reactant 2

HCID 109773182-(Dimethylaminomethyl)-4-(2-aminoethylthiomethyl)thiazoleHCID 13373520HCID 13373520, compound

Product 1

HCID 13373508HCID 13373508, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Following the procedure of Example 12, a mixture of 1.11 g. of 2-(2-dimethylaminomethyl-4-thiazolylmethylthio)ethylamine and 1.24 g. of 2-methylthio-5-(3-pyridyl)methyl-4-pyrimidinethione in 15 ml. of pyridine was refluxed for 2 days. The desired reaction product was purified by gradient elution high pressure liquid chromatography over silica using an ethyl acetate/ethanol/ammonium hydroxide solvent system as the eluant. Fractions shown by tlc to contain 2-[2-(2-dimethylaminomethyl-4-thiazolylmethylthio)ethyl]amino-5-(3-pyridyl)methyl-4-pyrimidinethione free base were combined and the solvent removed by evaporation.

Workup

  1. additiona mixture of 1.11 g
  2. customThe desired reaction product
  3. customwas purified by gradient elution high pressure liquid chromatography over silica using an ethyl acetate/ethanol/ammonium hydroxide solvent system as the eluant
  4. customthe solvent removed by evaporation

Sources & evidence

ORD record
ord-eb17eb6358af406a93f4cf06dcae4f2c
Source dataset
uspto-grants-1984_08
Patent number
US04468399

Reaction notes

Loading…