Dichloromethane → 5-Bromo-4-methylpyrimidin-2-amine

HRID 1043758Notes

Reaction equation

HRID 1043758 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>C(Cl)(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 3

HCID 6344DichloromethaneHCID 79392-Amino-4-methylpyrimidineHCID 67184N-bromobutanimide

Product 1

HCID 186161965-Bromo-4-methylpyrimidin-2-amineYield 100%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 4-methylpyrimidine-2-ylamine (10.9 g, 100 mmol) in chloroform (400 mL) was added N-bromosuccinimide (17.8 g, 100 mmol). The solution was stirred in the dark for 15 hours, at which time it was added to CH2Cl2 (1400 mL), washed with 1N NaOH (3×200 mL) and NaCl(sat.) (100 mL), dried over Na2SO4, filtered and concentrated, yielding 5-bromo-4-methylpyrimidine-2-ylamine (18.8 g, 99%). LCMS (m/z): 188.0/190.0 (MH+). 1H NMR (CDCl3): δ 8.22 (s, 1H), 5.02 (bs, 2H), 2.44 (s, 3H).

Workup

  1. washwashed with 1N NaOH (3×200 mL) and NaCl(sat.) (100 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ceb63e74e2ad4ce98e328f5fce0de40e
Source dataset
uspto-grants-2013_10
Patent number
US08563549B2

Reaction notes

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