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

HRID 358470Notes

Reaction equation

HRID 358470 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]([CH2:24][CH2:25][C:26]2[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=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]([CH2:24][CH2:25][C:26]3[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=3)=[CH:19][N:18]=2)[N:9]=1)[CH3:1]

Participants

4

Reactant 2

HCID 109773182-(Dimethylaminomethyl)-4-(2-aminoethylthiomethyl)thiazoleHCID 133735182-Methylthio-5-[2-(3-pyridyl)ethyl]-4-pyrimidone

Product 1

HCID 133735042-[2-(2-Dimethylaminomethyl-4-thiazolylmethylthio)ethyl]amino-5-[2-(3-pyridyl)ethyl]-4-pyrimidone

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 1.37 g. of 2-methylthio-5-[2-(3-pyridyl)ethyl]-4-pyrimidone in 25 ml. of anhydrous pyridine was heated to refluxing temperature for about 4 days. The solvent was removed in vacuo. The residue was dissolved in ethanol and the ethanol evaporated. The residue was purified by 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 the desired product were combined and the combined fractions rechromatographed on a silica preparative plate using 3% ammoniated ethanol as the solvent. 2-[2-(2-Dimethylaminomethyl-4-thiazolylmethylthio)ethyl]amino-5-[2-(3-pyridyl)ethyl]-4-pyrimidone free base thus prepared was converted by standard procedures to the trihydrochloride salt which melted at 226°-228° C. after recrystallization from an ethanol/ethyl acetate/ether solvent mixture. Yield=1.0 g.

Workup

  1. additiona mixture of 1.29 g
  2. temperatureto refluxing temperature for about 4 days
  3. customThe solvent was removed in vacuo
  4. dissolutionThe residue was dissolved in ethanol
  5. customthe ethanol evaporated
  6. customThe residue was purified by high pressure liquid chromatography over silica using
  7. washa gradient elution technique with an ethyl acetate/ethanol/ammonium hydroxide solvent system as the eluant
  8. customthe combined fractions rechromatographed on a silica preparative plate
  9. custom2-[2-(2-Dimethylaminomethyl-4-thiazolylmethylthio)ethyl]amino-5-[2-(3-pyridyl)ethyl]-4-pyrimidone free base thus prepared
  10. customafter recrystallization from an ethanol/ethyl acetate/ether solvent mixture

Sources & evidence

ORD record
ord-3a8cf7f1d86448ac9aba0c7964287a8b
Source dataset
uspto-grants-1984_08
Patent number
US04468399

Reaction notes

Loading…