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

HRID 1920817Notes

Reaction equation

HRID 1920817 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][N:3]=1.[Br:12]N1C(=O)CCC1=O.C(Cl)Cl.[OH-].[Na+]>C(Cl)(Cl)Cl>[Br:12][C:5]1[C:6]([C:8]([F:11])([F:9])[F:10])=[N:7][C:2]([NH2:1])=[N:3][CH:4]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 67184N-bromobutanimide2×HCID 5959152-Amino-4-(trifluoromethyl)pyrimidine

Product 1

HCID 453821525-Bromo-4-trifluoromethyl-pyrimidin-2-ylamineYield 91.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 2-amino-4-trifluoromethylpyrimidine (8.0 g, 49.1 mmol) in chloroform (300 mL) was added N-bromosuccinimide (8.9 g, 50 mmol). The solution was stirred in the dark for 16 hours, at which time additional N-bromosuccinimide (4.0 g, 22.5 mmol) was added. After stirring for an additional 4 hours the solution was added to CH2Cl2 (200 mL) and 1N NaOH (200 mL). Upon mixing, the layers were separated and the organic layer was washed with NaCl(sat.) (100 mL), dried over Na2SO4, filtered and concentrated, yielding 10.9 g (82%) of 5-bromo-4-(trifluoromethyl)-2-pyrimidylamine: LCMS (m/z): 242/244 (MH+); 1H NMR (CDCl3): δ 8.52 (s, 1H), 5.38 (bs, 2H).

Workup

  1. additionwas added
  2. additionUpon mixing
  3. customthe layers were separated
  4. washthe organic layer was washed with NaCl(sat.) (100 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-3ff4ae9a1f4f4627a547d6a1cd98376f
Source dataset
uspto-grants-2012_05
Patent number
US08173647B2

Reaction notes

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