Methylamine → 5-Bromo-2-chloro-4-methoxypyrimidine

HRID 2409088Notes

Reaction equation

HRID 2409088 reaction equation
[Br:1][C:2]1[C:3](Cl)=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.CN.C1C[O:15][CH2:14]C1>C(O)C>[Br:1][C:2]1[C:3]([O:15][CH3:14])=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 6329MethylamineHCID 8028TetrahydrofuranHCID 2899735-Bromo-2,4-dichloropyrimidine

Product 1

HCID 36631435-Bromo-2-chloro-4-methoxypyrimidineYield 76%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

To a cooled (−78° C.) solution of 5-bromo-2,4-dichloropyrimidine (1.7 g, 7.3 mmol) in THF (30 mL) was added dropwise a 25 wt % solution of methylamine in ethanol (1.7 mL). The reaction was allowed to warm to 0° C. and stirred for 1 h. The reaction was then concentrated and re-dissolved in EtOAc. The solution was washed with brine, dried over Na2SO4, filtered and concentrated to give 5-bromo-2-chloro-4-methoxypyrimidine (1.25 g, 76%). 1H-NMR (CDCl3): δ 8.43 (s, 1H), 4.10 (s, 3H).

Workup

  1. concentrationThe reaction was then concentrated
  2. dissolutionre-dissolved in EtOAc
  3. washThe solution was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-538c58cfb6da4e709927c5666550b478
Source dataset
uspto-grants-2014_08
Patent number
US08815882B2

Reaction notes

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