Methylamine → HCID 21996923, compound

HRID 1647679Notes

Reaction equation

HRID 1647679 reaction equation
[Cl:1][C:2]1[C:7]([O:8][CH:9]([F:11])[F:10])=[C:6]([F:12])[N:5]=[C:4](F)[N:3]=1.[CH3:14][NH2:15]>O1CCCC1>[Cl:1][C:2]1[C:7]([O:8][CH:9]([F:11])[F:10])=[C:6]([F:12])[N:5]=[C:4]([NH:15][CH3:14])[N:3]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 21996893HCID 21996893, compound

Product 1

HCID 21996923HCID 21996923, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

20.3 g (0.0938 mol) of 4-chlorodifluoromethoxy-2,6-difluoropyrimidine in 150 ml of tetrahydrofuran were initially taken and 5.8 g (0.188 mol) of gaseous methylamine were added at from -70° to -60° C. in the course of 30 minutes while stirring. Stirring was carried out for 1 hour at -70° C., for 1 hour at 0° C. and for 1 hour at 25° C. After the reaction mixture had been evaporated down under reduced pressure, the residue was stirred with water and extracted twice with ethyl acetate, and the extract was dried over magnesium sulfate. It was partially evaporated down under reduced pressure and then chromatographed over silica gel using 1:5 ether/petroleum ether. The first fractions contained the title compound of melting point 57°-61° C. in a yield of 12.5 g (58.5%).

Workup

  1. stirringStirring
  2. customAfter the reaction mixture had been evaporated down under reduced pressure
  3. stirringthe residue was stirred with water
  4. extractionextracted twice with ethyl acetate
  5. dry with materialthe extract was dried over magnesium sulfate
  6. customIt was partially evaporated down under reduced pressure
  7. customchromatographed over silica gel using 1:5 ether/petroleum ether

Sources & evidence

ORD record
ord-d50229fa6d864d2d9e8a7d1f0d0ccab3
Source dataset
uspto-grants-1995_07
Patent number
US05434124

Reaction notes

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