Methylamine → HCID 21996923, compound

HRID 232520Notes

Reaction equation

HRID 232520 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 continued for 1 hour in each case at -70° C., 0° C. and 25° C. The reaction mixture was evaporated down under reduced pressure, after which the residue was stirred with water, the solution was extracted twice with ethyl acetate and the extract was dried over magnesium sulfate. It was partially evaporated down under reduced pressure and then subjected to fractional chromatography 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. customThe reaction mixture was evaporated down under reduced pressure
  3. stirringafter which the residue was stirred with water
  4. extractionthe solution was extracted twice with ethyl acetate
  5. dry with materialthe extract was dried over magnesium sulfate
  6. customIt was partially evaporated down under reduced pressure

Sources & evidence

ORD record
ord-ceeae52fdca04aebb4435588bf4cd406
Source dataset
uspto-grants-1997_01
Patent number
US05591694

Reaction notes

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