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

HRID 1846170Notes

Reaction equation

HRID 1846170 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

Conditions

Temperature
23 °C

Procedure

To a stirred solution containing 4.31 g (34.8 mmol) of 2-amino-4,6-dimethylpyrimidine in 150 mL of acetonitrile was added 6.15 g (52.1 mmol) of N-bromosuccinimide. The reaction mixture was stirred at 23° C. for 3 h. The formed precipitate was filtered and dried to afford the expected product as a colorless solid: yield 5.93 g (83%); mp 183-185° C.; silica gel TLC Rf 0.15 (2:1 ethyl acetate-hexanes); 1H NMR (CDCl3) δ 2.44 (s, 6H) and 5.19 (br s, 2H); 13C NMR (CDCl3) δ 24.7, 24.7, 109.6, 160.7, 160.7 and 166.3; mass spectrum (APCI), m/z 201.9982 (M+H)+ (C6H9N3Br requires 201.9980).

Workup

  1. filtrationThe formed precipitate was filtered
  2. customdried

Sources & evidence

ORD record
ord-10e3b24e2dae488fa62e6ab3c56a55d3
Source dataset
uspto-grants-2015_02
Patent number
US08952025B2

Reaction notes

Loading…