Dichloromethane → 5-Bromo-4-trifluoromethyl-pyrimidin-2-ylamine

HRID 421310Notes

Reaction equation

HRID 421310 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:8]=[CH:7][N:6]=[C:5]([NH2:9])[N:4]=1.[Br:12]N1C(=O)CCC1=O.C(Cl)Cl.[OH-].[Na+]>C(Cl)(Cl)Cl>[Br:12][C:8]1[C:3]([C:2]([F:1])([F:10])[F:11])=[N:4][C:5]([NH2:9])=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 67184N-bromobutanimideHCID 5959152-Amino-4-(trifluoromethyl)pyrimidine

Product 1

HCID 453821525-Bromo-4-trifluoromethyl-pyrimidin-2-ylamineYield 75%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
50 °C

Procedure

4-(Trifluoromethyl)pyrimidin-2-ylamine (2 g, 12.3 mmol) was suspended in chloroform (70 ml) followed by the addition of N-bromosuccinimide (3.3 g, 18.4 mmol) and the resulting mixture was stirred at 50° C. for 5 hours and then at room temperature for 15 hours. A mixture of methylene chloride (50 ml) and 1 M sodium hydroxide (50 ml) was added, the resulting mixture was stirred, and then the organic layer was fractionated and dried over magnesium sulfate. The solvent was evaporated under reduced pressure to give the title compound (2.2 g, 75%) as a pale orange solid.

Workup

  1. waitat room temperature for 15 hours
  2. additionwas added
  3. stirringthe resulting mixture was stirred
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-263954a018de4e44a9c107e09e917c3a
Source dataset
uspto-grants-2012_01
Patent number
US08097622B2

Reaction notes

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