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

HRID 2202817Notes

Reaction equation

HRID 2202817 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+].O>CN(C=O)C>[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

6

Reactant 4

HCID 962WaterHCID 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-methylpyrimidineYield 69%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4,6-dichloro-2-methylpyrimidine (2-1) (137.8 g, 845 mmol), 3,5-dimethyl-1H-1,2,4-triazole (2-2) (82 g, 845 mmol), and Cs2CO3 (275 g, 845 mmol) were suspended in DMF (1 L) and the resulting mixture was stirred at room temperature for 66 h. The mixture was then poured into water (2 L) and stirred for 1 hour. The precipitate was filtered, washed with water (2×) and dried under vacuum to afford Intermediate 2 as an off-white solid (130 g, 69%). MS: m/z=224.2 (M+H).

Workup

  1. stirringstirred for 1 hour
  2. filtrationThe precipitate was filtered
  3. washwashed with water (2×)
  4. customdried under vacuum

Sources & evidence

ORD record
ord-1f8731c7f7a842739298a980d3b853d3
Source dataset
uspto-grants-2016_06
Patent number
US09365562B2

Reaction notes

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