2-Amino-4-chloro-6-methylpyrimidine → 5-Bromo-4-chloro-6-methylpyrimidin-2-amine

HRID 2389992Notes

Reaction equation

HRID 2389992 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([Cl:8])[CH:5]=[C:4]([CH3:9])[N:3]=1.[Br:10]Br>ClCCl>[Br:10][C:5]1[C:6]([Cl:8])=[N:7][C:2]([NH2:1])=[N:3][C:4]=1[CH3:9]

Participants

4

Reactant 2

HCID 218102-Amino-4-chloro-6-methylpyrimidineHCID 24408Bromine

Product 1

HCID 2370085-Bromo-4-chloro-6-methylpyrimidin-2-amineYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of the 2-amino-4-chloro-6-methylpyrimidine (5.00 g, 34.8 mmol) in dichloromethane (240 mL) was added bromine (1.88 mL, 36.6 mmol). The resulting suspension was stirred at room temperature for 1.5 hours. The mixture was diluted with dichloromethane (1.3 L) and washed with saturated sodium bicarbonate (2×200 mL) and brine (200 mL), dried (MgSO4), filtered and concentrated to afford 5-bromo-4-chloro-6-methylpyrimidin-2-amine (7.5 g, 97%).

Workup

  1. washwashed with saturated sodium bicarbonate (2×200 mL) and brine (200 mL)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c6278e8b194c445b8f5a1925a86604a5
Source dataset
uspto-grants-2012_09
Patent number
US08273755B2

Reaction notes

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