tert-Butoxy bis(dimethylamino)methane → HCID 59185797, compound

HRID 1951246Notes

Reaction equation

HRID 1951246 reaction equation
[C:1]([C:4]1[C:5]([CH3:15])=[C:6]2[C:11](=[O:12])[NH:10][CH2:9][CH2:8][N:7]2[C:13]=1[CH3:14])(=[O:3])[CH3:2].CC(O[CH:21](N(C)C)[N:22]([CH3:24])[CH3:23])(C)C>CC(C)=O>[CH3:21][N:22]([CH3:24])/[CH:23]=[CH:2]/[C:1]([C:4]1[C:5]([CH3:15])=[C:6]2[C:11](=[O:12])[NH:10][CH2:9][CH2:8][N:7]2[C:13]=1[CH3:14])=[O:3]

Participants

4

Reactant 2

HCID 79885tert-Butoxy bis(dimethylamino)methaneHCID 59185808HCID 59185808, compound

Product 1

HCID 59185797HCID 59185797, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
95 °C

Procedure

7-Acetyl-6,8-dimethyl-3,4-dihydro-2H-pyrrolo[1,2-a]pyrazin-1-one (6.692 g, 32.49 mmol) was combined with Brederick's reagent (13.42 mL, 64.98 mmol) and heated to 95° C. for 10 hours. After cooling the reaction mixture was treated with acetone (2 mL) and the resulting yellow precipitate filtered off and washed with 2:1 EtOAc:Me2CO to provide the target compound (6.496 g, 24.86 mmol, 77% yield).

Workup

  1. temperatureAfter cooling the reaction mixture
  2. filtrationthe resulting yellow precipitate filtered off
  3. washwashed with 2:1 EtOAc

Sources & evidence

ORD record
ord-9618cff7d9424619a30e052a5675f6f3
Source dataset
uspto-grants-2013_03
Patent number
US08404692B2

Reaction notes

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