2-Amino-4-methylpyrimidine → 5-Bromo-4-methylpyrimidin-2-amine

HRID 334110Notes

Reaction equation

HRID 334110 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH2:8])[N:3]=1.[Br:9]N1C(=O)CCC1=O>C(Cl)(Cl)Cl.C(Cl)Cl>[Br:9][C:7]1[C:2]([CH3:1])=[N:3][C:4]([NH2:8])=[N:5][CH:6]=1

Participants

5

Reactant 2

HCID 79392-Amino-4-methylpyrimidineHCID 67184N-bromobutanimide

Product 1

HCID 186161965-Bromo-4-methylpyrimidin-2-amineYield 87.4%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-methylpyrimidine-2-ylamine (8.0 g, 0.073 mol) in chloroform (320 mL) was added N-bromosuccinimide (13.7 g, 0.077 mol). The reaction mixture was stirred in the dark for 18 hrs. LC/MS indicated the reaction was completed. The mixture was diluted with DCM, then washed with 1N NaOH aq solution and brine, dried over MgSO4, filtered and concentrated to yield 5-bromo-4-methylpyrimidine-2-ylamine (12 g, Yield: 86%).

Workup

  1. washwashed with 1N NaOH aq solution and brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-6c5e31e73b2b4499b7f2cd2174c545ab
Source dataset
uspto-grants-2014_11
Patent number
US08883799B2

Reaction notes

Loading…