Cesium carbonate → 4-chloro-6-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-2-methylpyrimidine

HRID 925423

Reaction equation

HRID 925423 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([CH3:9])[N:3]=1.[CH3:10][C:11]1[N:15]=[C:14]([CH3:16])[NH:13][N:12]=1.C([O-])([O-])=O.[Cs+].[Cs+]>C1COCC1>[Cl:8][C:6]1[CH:7]=[C:2]([N:12]2[C:11]([CH3:10])=[N:15][C:14]([CH3:16])=[N:13]2)[N:3]=[C:4]([CH3:9])[N:5]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 1390011H-1,2,4-Triazole, 3,5-dimethyl-HCID 2349974,6-Dichloro-2-methylpyrimidine

Product 1

HCID 624817454-chloro-6-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-2-methylpyrimidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4,6-dichloro-2-methylpyrimidine (505 mg, 3.1 mmol), 3,5-dimethyl-1H-1,2,4-triazole (300 mg, 3.1 mmol) and Cs2CO3 (1.54 g, 4.7 mmol) in THF (20 mL) was heated at reflux overnight. The mixture was filtered and the filtrate was concentrated to give 4-chloro-6-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-2-methylpyrimidine that was used without further purification. MS: m/z=224.1 (M+H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. filtrationThe mixture was filtered
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-df635fc5261f49109ebdfc55dd0943a2
Source dataset
uspto-grants-2016_03
Patent number
US09284302B2

Linked notes

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