Methylamine → HCID 21996923, compound

HRID 1197413Notes

Reaction equation

HRID 1197413 reaction equation
[CH3:1][NH2:2].[Cl:3][C:4]1[C:9]([O:10][CH:11]([F:13])[F:12])=[C:8]([F:14])[N:7]=[C:6](F)[N:5]=1>O1CCCC1>[Cl:3][C:4]1[C:9]([O:10][CH:11]([F:13])[F:12])=[C:8]([F:14])[N:7]=[C:6]([NH:2][CH3:1])[N:5]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 21996893HCID 21996893, compound

Product 1

HCID 21996923HCID 21996923, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

At -70° to -60° C. and over a period of 30 minutes, 5.8 g (0.188 mol) of gaseous methylamine was added, with stirring, to 20.3 g (0.0938 mol) of 4-chlorodifluoromethoxy-2,6-difluoropyrimidine in 150 ml of tetrahydrofuran. The mixture was stirred for 1 hour at -70° C., 1 hour at 0° C. and 1 hour at 25° C., and then 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 evaporated down, partially under reduced pressure, and then fractionally chromatographed over silica gel (1:5 ether/ligroin mixture). The first fractions contained the title compound (melting point 57°-61° C.) in a yield of 12.5 g (58.5%).

Workup

  1. customevaporated down under reduced pressure
  2. stirringThe residue was stirred with water
  3. extractionextracted twice with ethyl acetate
  4. dry with materialthe extract was dried over magnesium sulfate
  5. customIt was evaporated down, partially under reduced pressure
  6. customfractionally chromatographed over silica gel (1:5 ether/ligroin mixture)

Sources & evidence

ORD record
ord-bea91986865e456b90e392752f70fabe
Source dataset
uspto-grants-1994_01
Patent number
US05276007

Reaction notes

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