Dimethylamine → 5-bromo-4-methoxy-N,N-dimethylpyrimidin-2-amine
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]=1Participants
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
- customTo get more product
- customreaction mixture
- stirringwas stirred at RT for 1 hour
- concentrationThe mixture was concentrated
- additionthe crude was diluted in EtOAc/brine
- extractionextracted
- extractionthe organic extract
- dry with materialwas dried (Na2SO4)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-9cbd94a1c0184195aefc9e5751c1b429
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09403827B2
Reaction notes
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