Sodium hydride → 1-(2-methylsulfanyl-pyrimidin-4-yl)-1H-benzotriazol-4-ylamine

HRID 1516432Notes

Reaction equation

HRID 1516432 reaction equation
[NH2:1][C:2]1[C:10]2[N:9]=[N:8][NH:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Cl[C:14]1[CH:19]=[CH:18][N:17]=[C:16]([S:20][CH3:21])[N:15]=1>CN(C=O)C>[CH3:21][S:20][C:16]1[N:17]=[C:18]([N:7]2[C:6]3[CH:5]=[CH:4][CH:3]=[C:2]([NH2:1])[C:10]=3[N:9]=[N:8]2)[CH:19]=[CH:14][N:15]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 971134-Chloro-2-methylthiopyrimidineHCID 178507462HCID 178507462, compound

Product 1

HCID 674350661-(2-methylsulfanyl-pyrimidin-4-yl)-1H-benzotriazol-4-ylamineYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Dry DMF (100 mL) was cooled under N2 in an ice bath. To this was added 4-amino-1H-benzotriazole (9.0 g), and the mixture stirred for 10 min. To this was added NaH (60%, 2.95 g), and the mixture stirred on the ice bath for 15 min. Finally, 4-chloro-2-methylsulfanyl-pyrimidine (11.00 g) was added, the ice bath removed, the mixture allowed to warm to RT, and then heated to 85° C. for 1 h. The reaction mixture was then cooled to RT, and diluted with ice water. The fine yellow precipitate was filtered, washed with cold water, and titurated with EtOAc to provide 1-(2-methylsulfanyl-pyrimidin-4-yl)-1H-benzotriazol-4-ylamine (13.43 g, 78% yield).

Workup

  1. customthe ice bath removed
  2. temperatureheated to 85° C. for 1 h
  3. temperatureThe reaction mixture was then cooled to RT
  4. additiondiluted with ice water
  5. filtrationThe fine yellow precipitate was filtered
  6. washwashed with cold water

Sources & evidence

ORD record
ord-48c825e60df44196a896d869e70c3a71
Source dataset
uspto-grants-2012_07
Patent number
US08227478B2

Reaction notes

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