Dichloromethane → 2-Amino-5-bromo-4-methoxypyrimidine

HRID 1512094Notes

Reaction equation

HRID 1512094 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([NH2:9])[N:4]=1.[Br:10]N1C(=O)CCC1=O.C(Cl)Cl.[OH-].[Na+]>C(Cl)(Cl)Cl>[Br:10][C:8]1[C:3]([O:2][CH3:1])=[N:4][C:5]([NH2:9])=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 67184N-bromobutanimideHCID 674284-Methoxy-2-pyrimidinamine

Product 1

HCID 450369372-Amino-5-bromo-4-methoxypyrimidineYield 96%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 4-methoxypyrimidine-2-ylamine (1.84 g, 14.7 mmol) in chloroform (600 mL) was added N-bromosuccinimide (2.62 g, 14.7 mmol). After stirring in the dark for 5 hours, the solution was added to CH2Cl2 (200 mL) and 1N NaOH (100 mL). Upon mixing, the layers were separated and the organic layer was washed with NaCl(sat.) (100 mL), dried over Na2SO4, filtered and concentrated yielding 2.88 g (96%) of 5-bromo-4-methoxypyrimidine-2-ylamine. LCMS (m/z): 204/206 (MH+). 1H NMR (CDCl3): δ 8.10 (s, 1H), 4.93 (bs, 2H), 3.96 (s, 3H).

Workup

  1. additionUpon mixing
  2. customthe layers were separated
  3. washthe organic layer was washed with NaCl(sat.) (100 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-61bf42beee9843c794f345f6fb5a084c
Source dataset
uspto-grants-2012_07
Patent number
US08217035B2

Reaction notes

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