Dimethylformamide → HCID 59718927, compound

HRID 1852530Notes

Reaction equation

HRID 1852530 reaction equation
[H-].[Na+].CN(C=O)C.[NH:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[N:9]1.Cl[C:18]1[CH:23]=[CH:22][N:21]=[C:20]([S:24][CH3:25])[N:19]=1>O>[CH3:25][S:24][C:20]1[N:21]=[C:22]([N:8]2[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[N:10]=[N:9]2)[CH:23]=[CH:18][N:19]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 971134-Chloro-2-methylthiopyrimidineHCID 178418385HCID 178418385, compound

Product 1

HCID 59718927HCID 59718927, compoundYield 74.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 1 L round bottom flask was loaded with sodium hydride dispersion (10.0 g, 250 mmol, 60% in mineral oil) and 200 mL of DMF, and the resulting slurry cooled with an ice bath. Benzotriazole (18.02 g, 151 mmol) was added portionwise over a 10-12 min period. The reaction mixture was stirred for 10 min to allow gas evolution to subside; the ice bath was then removed and 4-chloro-2-methylthiopyrimidine (24.07 g, 150 mmol) was added. The resulting mixture was stirred at RT for 15 minutes, then placed in a 90° C. oil bath for 1.5 hour. The heating bath was turned off and the reaction mixture was allowed to slowly cool with stirring overnight. The reaction mixture was then poured into 500 mL of water and stirred for 20 min, and then filtered. The collected solids were washed with 3 portions of water and 3 portions of a mixture of hexanes/EtOAc (10:1 to 5:1), then dried to give 1-(2-methylsulfanyl-pyrimidin-4-yl)-1H-benzotriazole as an off-white solid (27.05 g, 74% yield), mp=180.5-181.7° C.; MS=244 (M+H)+.

Workup

  1. temperaturethe resulting slurry cooled with an ice bath
  2. customthe ice bath was then removed
  3. stirringThe resulting mixture was stirred at RT for 15 minutes
  4. customplaced in a 90° C.
  5. customfor 1.5 hour
  6. temperatureto slowly cool
  7. stirringwith stirring overnight
  8. stirringstirred for 20 min
  9. filtrationfiltered
  10. washThe collected solids were washed with 3 portions of water and 3 portions of a mixture of hexanes/EtOAc (10:1 to 5:1)
  11. customdried

Sources & evidence

ORD record
ord-5adf25b8f743478a8d19b13e0d5497f2
Source dataset
uspto-grants-2015_02
Patent number
US08962622B2

Reaction notes

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