Potassium Carbonate → 3-[2-(4-(Pyrimidin-2-yl)piperazin-1-yl)ethylmercapto]1,2,4-triazolo(4,3-a)pyridine

HRID 476911Notes

Reaction equation

HRID 476911 reaction equation
[N:1]1([CH2:7][CH2:8][S:9][C:10]2[N:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]3=[N:12][N:11]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Cl[C:20]1[N:25]=[CH:24][CH:23]=[CH:22][N:21]=1.C(=O)([O-])[O-].[K+].[K+]>C(O)(C)C>[N:21]1[CH:22]=[CH:23][CH:24]=[N:25][C:20]=1[N:4]1[CH2:3][CH2:2][N:1]([CH2:7][CH2:8][S:9][C:10]2[N:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]3=[N:12][N:11]=2)[CH2:6][CH2:5]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 744042-ChloropyrimidineHCID 198371223-[2-(Piperazin-1-yl)ethylmercapto]1,2,4-triazolo(4,3-a)pyridine

Product 1

HCID 198370983-[2-(4-(Pyrimidin-2-yl)piperazin-1-yl)ethylmercapto]1,2,4-triazolo(4,3-a)pyridineYield 45%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

4.8 g of 3-[2-(piperazin-1-yl)ethylmercapto]1,2,4-triazolo(4,3-a)pyridine, prepared in Example 79, and 2.1 g of 2-chloropyrimidine are heated under reflux in 140 ml of isopropanol in the presence of 2.5 g of potassium carbonate. After heating for 2 hours, the medium is cooled, the mineral substances are filtered off and the filtrate is concentrated. The oily residue is filtered on silica gel (eluent: chloroform/methanol 90/10). The resulting residue crystallizes from an ethyl ether/isopropyl ether mixture to give 2.8 g of 3-[2-(4-(pyrimidin-2-yl)piperazin-1-yl)ethylmercapto]1,2,4-triazolo(4,3-a)pyridine in the form of crystals melting at 126°-7° C.

Workup

  1. temperatureare heated
  2. temperatureAfter heating for 2 hours
  3. temperaturethe medium is cooled
  4. filtrationthe mineral substances are filtered off
  5. concentrationthe filtrate is concentrated
  6. filtrationThe oily residue is filtered on silica gel (eluent: chloroform/methanol 90/10)
  7. customThe resulting residue crystallizes from an ethyl ether/isopropyl ether mixture

Sources & evidence

ORD record
ord-9d70643943e6446daa146323d529c3a1
Source dataset
uspto-grants-1989_12
Patent number
US04886805

Reaction notes

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