Pyridine → 5,7-dimethyl-N-(2,6-dimethylphenyl)-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide

HRID 477235Notes

Reaction equation

HRID 477235 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]2[N:9]=[C:10]([S:12](Cl)(=[O:14])=[O:13])[N:11]=[C:4]2[N:3]=1.[CH3:16][C:17]1[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[C:18]=1[NH2:19].N1C=CC=CC=1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]2[N:9]=[C:10]([S:12]([NH:19][C:18]3[C:20]([CH3:24])=[CH:21][CH:22]=[CH:23][C:17]=3[CH3:16])(=[O:14])=[O:13])[N:11]=[C:4]2[N:3]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 68962,6-DimethylanilineHCID 6112325,7-Dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-sulfonyl chloride

Product 1

HCID 141551445,7-dimethyl-N-(2,6-dimethylphenyl)-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamideYield 97.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 2.2 g (8.9 mmol) of 5,7-dimethyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl chloride, 1.01 ml (8.4 mmol) of 2,6-dimethylaniline, 0.7 ml (8.4 mmol) of dry pyridine and 4 mg of DMAP in 20 ml of CH2Cl2 was stirred at room temperature for 17 hours. The solvent was removed by evaporation and the residue was taken up in 0.5M NaOH. The solution was extracted with diethyl ether and the aqueous phase was acidified with 3N HCl to precipitate a solid. The solid was collected by filtration and dried in vacuo to yield 2.72 g (97 percent) of the desired product as a white solid, m.p. 263°-266° C. (decomp.): 1H NMR (DMSO-d6)δ10.4 (1H, broad S), 7.55 (1H, s), 7.2 (3H, s), 2.7 and 2.8 (3H each, s) and 2.1 (6H, s); IR (KBr) 3100, 2980-2780, 1628, 1540 and 1355 cm-1.

Workup

  1. customThe solvent was removed by evaporation
  2. extractionThe solution was extracted with diethyl ether
  3. customto precipitate a solid
  4. filtrationThe solid was collected by filtration
  5. customdried in vacuo

Sources & evidence

ORD record
ord-e8ca3bcfbdfe4708a6be2006ae0d37b7
Source dataset
uspto-grants-1989_12
Patent number
US04886883

Reaction notes

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