2-Amino-4,6-dimethyl pyrimidine → 2-Amino-5-bromo-4,6-dimethylpyrimidine

HRID 1846139Notes

Reaction equation

HRID 1846139 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[N:3]=1.[Br:10]N1C(=O)CCC1=O>C(#N)C>[NH2:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([Br:10])=[C:4]([CH3:9])[N:3]=1

Participants

4

Reactant 2

HCID 130212-Amino-4,6-dimethyl pyrimidineHCID 67184N-bromobutanimide

Product 1

HCID 27377352-Amino-5-bromo-4,6-dimethylpyrimidine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution containing 4.31 g (34.75 mmol) of 2-amino-4,6-dimethylpyrimidine (2) in 150 mL of acetonitrile were added 6.15 g (52.12 mmol) of N-bromosuccinimide. The reaction mixture was stirred at room temperature under argon atmosphere for 3 h. The formed precipitate was filtered and dried to afford the expected product as a white solid: yield 5.93 g (83%). 1H-NMR (CDCl3) δ 5.19 (br, 2H), 2.44 (s, 6H); 13C-NMR (CDCl3) δ 166.28, 160.73, 109.60, 24.70.

Workup

  1. filtrationThe formed precipitate was filtered
  2. customdried

Sources & evidence

ORD record
ord-c05991a7678c4ab79fee7943cc5faf17
Source dataset
uspto-grants-2015_02
Patent number
US08952025B2

Reaction notes

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