2-(Dimethylaminomethyl)-4-(2-aminoethylthiomethyl)thiazole → HCID 13373486, compound

HRID 358465Notes

Reaction equation

HRID 358465 reaction equation
CN(CC1SC=C(CSCCN)N=1)C.[N+](NC1NC(=O)C(CC2C=CC=CN=2)=CN=1)([O-])=O.Cl.Cl.Cl.[CH3:36][N:37]([CH2:39][C:40]1[S:41][CH:42]=[C:43]([CH2:45][S:46][CH2:47][CH2:48][NH:49][C:50]2[NH:55][C:54](=[O:56])[C:53]([CH2:57][C:58]3[CH:63]=[CH:62][CH:61]=[CH:60][N:59]=3)=[CH:52][N:51]=2)[N:44]=1)[CH3:38]>C(O)C>[CH3:36][N:37]([CH2:39][C:40]1[S:41][CH:42]=[C:43]([CH2:45][S:46][CH2:47][CH2:48][NH:49][C:50]2[NH:55][C:54](=[O:56])[C:53]([CH2:57][C:58]3[CH:63]=[CH:62][CH:61]=[CH:60][N:59]=3)=[CH:52][N:51]=2)[N:44]=1)[CH3:38]

Participants

5

Reactant 3

HCID 109773182-(Dimethylaminomethyl)-4-(2-aminoethylthiomethyl)thiazoleHCID 13373475HCID 13373475, compoundHCID 13373487HCID 13373487, compound

Product 1

HCID 13373486HCID 13373486, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Following the procedure of Example 1, a reaction mixture was prepared from 1.62 g. of 2-(2-dimethylaminomethyl-4-thiazolylmethylthio)ethylamine, 1.73 g. of 2-nitroamino-5-(2-pyridyl)methyl-4-pyrimidone and 20 ml. of ethanol. The reaction mixture was heated at refluxing temperature for about 21 hours. The solvents were removed in vacuo and the residue purified by high pressure liquid gradient elution chromatography (silica-ethanol/ethyl acetate/ammonium hydroxide). Fractions containing 2-[2-(2-dimethylaminomethyl-4-thiazolylmethylthio)ethyl-amino-5-(2-pyridyl)methyl-4-pyrimidone (as determined by TLC) were combined and the solvents removed from the combined fractions by evaporation. The resulting crystalline residue was dissolved in ethanol and a slight excess of 5N aqueous hydrochloric acid added. The reaction mixture was evaporated to dryness and the resulting crystalline residue recrystallized from a mixture of methanol and ethanol to yield 1.2 g. of 2-[2-(2-dimethylaminomethyl-4-thiazolylmethylthio)ethyl]amino-5-(2-pyridyl)methyl-4-pyrimidone trihydrochloride melting at 205°-207° C.

Workup

  1. customa reaction mixture was prepared from 1.62 g
  2. temperatureThe reaction mixture was heated
  3. temperatureat refluxing temperature for about 21 hours
  4. customThe solvents were removed in vacuo
  5. customthe residue purified by high pressure liquid gradient elution chromatography (silica-ethanol/ethyl acetate/ammonium hydroxide)
  6. additionFractions containing 2-[2-(2-dimethylaminomethyl-4-thiazolylmethylthio)ethyl-amino-5-(2-pyridyl)methyl-4-pyrimidone (as determined by TLC)
  7. customthe solvents removed from the combined fractions by evaporation
  8. dissolutionThe resulting crystalline residue was dissolved in ethanol
  9. additiona slight excess of 5N aqueous hydrochloric acid added
  10. customThe reaction mixture was evaporated to dryness
  11. customthe resulting crystalline residue recrystallized from a mixture of methanol and ethanol
  12. customto yield 1.2 g

Sources & evidence

ORD record
ord-292ffa178aba4286afc631ea41b12f5b
Source dataset
uspto-grants-1984_08
Patent number
US04468399

Reaction notes

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