2-(Dimethylaminomethyl)-4-(2-aminoethylthiomethyl)thiazole → HCID 13373510, compound

HRID 358469Notes

Reaction equation

HRID 358469 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](=[O:23])[C:20]([O:24][C:25]2[CH:26]=[N:27][C:28]([CH3:31])=[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](=[O:23])[C:20]([O:24][C:25]3[CH:26]=[N:27][C:28]([CH3:31])=[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 13373517HCID 13373517, compound

Product 1

HCID 13373510HCID 13373510, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Following the procedure of Example 12, a mixture of 1.29 g. of 2-(2-dimethylaminomethyl-4-thiazolylmethylthio)ethylamine and 1.38 g. of 2-methylthio-5-(6-methyl-3-pyridyl)oxy-4-pyrimidone in pyridine solution were heated to refluxing temperature for about 88 hours. After this time, the solvent was removed by evaporation in vacuo and the residue dissolved in ethanol. The ethanolic solution was evaporated to dryness. The residue was subjected to high pressure liquid chromatography over silica using a gradient elution technique with 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-(6-methyl-3-pyridyl)oxy-4-pyrimidone were combined and the solvent removed by evaporation. The resulting residue was rechromatographed on a silica preparative plate using 3% ammoniated ethanol as the solvent. 2-[2-(2-Dimethylaminomethyl-4-thiazolylmethylthio)ethyl]amino-5-(6-methyl-3-pyridyl)oxy-4-pyrimidone free base thus obtained was converted to the corresponding trihydrochloride salt by standard procedures. 2-[2-(2-Dimethylaminomethyl-4-thiazolylmethylthio)ethyl]amino-5-(6-methyl-3-pyridyl)oxy-4-pyrimidone trihydrochloride melted at about 216°-220° C. after recrystallization from a mixture of ethanol, ethyl acetate and ether. Yield=0.36 g.

Workup

  1. additiona mixture of 1.29 g
  2. temperatureto refluxing temperature for about 88 hours
  3. customAfter this time, the solvent was removed by evaporation in vacuo
  4. dissolutionthe residue dissolved in ethanol
  5. customThe ethanolic solution was evaporated to dryness
  6. washa gradient elution technique with an ethyl acetate/ethanol/ammonium hydroxide solvent system as the eluant
  7. customthe solvent removed by evaporation
  8. customThe resulting residue was rechromatographed on a silica preparative plate

Sources & evidence

ORD record
ord-5fcfb6e895564bad804c0e28730f5e44
Source dataset
uspto-grants-1984_08
Patent number
US04468399

Reaction notes

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