Dimethylamine → 5-bromo-4-methoxy-N,N-dimethylpyrimidin-2-amine

HRID 1478244Notes

Reaction equation

HRID 1478244 reaction equation
[Br:1][C:2]1[C:3]([O:9][CH3:10])=[N:4][C:5](Cl)=[N:6][CH:7]=1.[CH3:11][NH:12][CH3:13]>>[Br:1][C:2]1[C:3]([O:9][CH3:10])=[N:4][C:5]([N:12]([CH3:13])[CH3:11])=[N:6][CH:7]=1

Participants

3

Procedure

224 ml (448 mmol) of dimethylamine was added to a solution of 50 g (224 mmol) 5-bromo-2-chloro-4-methoxypyrimidine at RT and the solution was stirred at RT for 72 hours. To get more product, another 40 ml dimethylamine were added and reaction mixture was stirred at RT for 1 hour. The mixture was concentrated and the crude was diluted in EtOAc/brine, extracted and the organic extract was dried (Na2SO4) and concentrated to afford 51.79 g (223 mmol) of the title compound as a white solid. LCMS: (M+H)=231/233; tR=1.02 min (LC-MS 4). 1H-NMR (d6-DMSO, 400 MHz) 8.17 (s, 1H) 3.89 (s, 3H) 3.07 (s, 6H).

Workup

  1. customTo get more product
  2. customreaction mixture
  3. stirringwas stirred at RT for 1 hour
  4. concentrationThe mixture was concentrated
  5. additionthe crude was diluted in EtOAc/brine
  6. extractionextracted
  7. extractionthe organic extract
  8. dry with materialwas dried (Na2SO4)
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-9cbd94a1c0184195aefc9e5751c1b429
Source dataset
uspto-grants-2016_08
Patent number
US09403827B2

Reaction notes

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