Tert-Butylamine → HCID 15544682, compound

HRID 650910Notes

Reaction equation

HRID 650910 reaction equation
Br[C:2]1[C:11]([N:12]2[C:17](=[O:18])[CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[N:14]([CH3:23])[C:13]2=[O:24])=[C:10](C)[CH:9]=[C:8]([Cl:26])[C:3]=1[C:4]([O:6]C)=O.[C:27]([NH2:31])([CH3:30])([CH3:29])[CH3:28].[CH2:32]1COCC1>>[Cl:26][C:8]1[CH:9]=[CH:10][C:11]([N:12]2[C:17](=[O:18])[CH:16]=[C:15]([C:19]([F:20])([F:22])[F:21])[N:14]([CH3:23])[C:13]2=[O:24])=[C:2]2[C:3]=1[C:4](=[O:6])[N:31]([C:27]([CH3:30])([CH3:29])[CH3:28])[CH2:32]2

Participants

4

Reactant 3

HCID 6385Tert-ButylamineHCID 8028TetrahydrofuranHCID 86757256HCID 86757256, compound

Product 1

HCID 15544682HCID 15544682, compound

Procedure

A solution of 0.50 gram (0.0011 mole) of methyl 2-bromo-methyl-6-chloro-3-[1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedion-3-yl]benzoate and 0.18 gram (0.0025 mole) of tert.-butylamine in 50 mL of THF was stirred at ambient temperature for about 18 hours. After this time, TLC analysis of the reaction mixture indicated little reaction had taken place. The reaction mixture was warmed to reflux where it stirred for an additional 18 hours, then it was concentrated under reduced pressure to a residue. The residue was taken up in methylene chloride and washed in turn with water and an aqueous solution saturated with sodium chloride. The organic layer was dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to a residue. The residue was purified by column chromatography on silica gel using mixtures of EtOAc and hexane as eluants. The fractions containing product were combined and concentrated under reduced pressure, yielding 0.36 gram of subject compound. The NMR spectrum was consistent with the proposed structure.

Workup

  1. customreaction
  2. temperatureThe reaction mixture was warmed
  3. temperatureto reflux where it
  4. concentrationit was concentrated under reduced pressure to a residue
  5. washwashed in turn with water
  6. dry with materialThe organic layer was dried with magnesium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated under reduced pressure to a residue
  9. customThe residue was purified by column chromatography on silica gel using mixtures of EtOAc and hexane as eluants
  10. additionThe fractions containing product
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-34718de938d1480e8f512b221989b9ce
Source dataset
uspto-grants-2001_08
Patent number
US06277847B1

Reaction notes

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