Diisopropylamine → HCID 22451777, compound

HRID 2186041Notes

Reaction equation

HRID 2186041 reaction equation
C(N[CH:5]([CH3:7])[CH3:6])(C)C.[CH2:8]([Li])CCC.[CH3:13][C:14]1[CH:19]=[N:18][CH:17]=[CH:16][N:15]=1.Br[CH2:21][C:22]([O:24]CCCC)=[O:23]>C1COCC1>[N:15]1[CH:16]=[CH:17][N:18]=[CH:19][C:14]=1[CH2:13][CH2:21][C:22]([O:24][C:5]([CH3:6])([CH3:7])[CH3:8])=[O:23]

Participants

6

Reactant 4

HCID 7912DiisopropylamineHCID 79762-MethylpyrazineHCID 87883Butyl bromoacetateHCID 178418339Butyllithium

Product 1

HCID 22451777HCID 22451777, compoundYield 67.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of diisopropylamine (4.0 mL, 28.5 mmol) in THF (20 mL) was treated with 2.5M n-butyllithium (11.42 mL, 28.5 mmol) at −78° C. The mixture was warmed to RT for 0.5 h, cooled to −78° C., and 2-methylpyrazine (2.0 mL, 21.9 mmol) was added. The reaction mixture was warmed to RT, stirred for 1 h, cooled to −78° C., and butyl bromoacetate (4.25 mL, 26.3 mmol) was added. The reaction mixture was warmed to RT, stirred for 18 h and quenched with water (1 mL). The mixture was concentrated and the residue was purified by flash chromatography (silica gel, 60% ethyl acetate/hexane) to give the title compound (3.06 g, 67%) as a light yellow oil. MS(ES) m/e 209 [M+H]+; 1H NMR (250 MHz) δ8.37-8.57 (m, 3H), 3.10 (t, 2H), 2.74 (t, 2H), 1.43 (s, 9H).

Workup

  1. temperaturecooled to −78° C.
  2. temperatureThe reaction mixture was warmed to RT
  3. temperaturecooled to −78° C.
  4. temperatureThe reaction mixture was warmed to RT
  5. stirringstirred for 18 h
  6. customquenched with water (1 mL)
  7. concentrationThe mixture was concentrated
  8. customthe residue was purified by flash chromatography (silica gel, 60% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-a97ca475d0474e99aa72a82d77b54b96
Source dataset
uspto-grants-2002_06
Patent number
US06403578B1

Reaction notes

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