Sodium Carbonate → 3-(5-Aminopyrazin-2-yl)cyclopent-2-enone

HRID 595852Notes

Reaction equation

HRID 595852 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH2:13][CH2:12][C:11](=[O:14])[CH:10]=2)O1.[NH2:16][C:17]1[CH:22]=[N:21][C:20](Br)=[CH:19][N:18]=1.C([O-])([O-])=O.[Na+].[Na+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl.O>[NH2:16][C:17]1[N:18]=[CH:19][C:20]([C:9]2[CH2:13][CH2:12][C:11](=[O:14])[CH:10]=2)=[N:21][CH:22]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 5995392-Amino-5-bromopyrazineHCID 668228763-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-cyclopenten-1-one

Product 1

HCID 1180456313-(5-Aminopyrazin-2-yl)cyclopent-2-enone

Reagents, catalysts & solvents 2

HCID 178418807HCID 178418807, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclopent-2-enone (2.99 g, 14.37 mmol) (the filtrate from last step) was added 2-amino-5 bromopyrazine (2.5 g, 14.37 mmol), PdCl2(dppf)-CH2Cl2 (1.173 g, 1.437 mmol), Na2CO3 (7.61 g, 71.8 mmol) and water (17.96 mL) the reaction mixture was stirred at 100° C. oil bath for overnight, filtered through Celite. The reaction mixture was then extracted by EtOAc. The organic was then used 3N HCl (20 mL) washed 2 times, and water 50 mL once, the AQ was then neutralized by NaOH to pH=8, the reaction mixture was then extracted by CHCl3/IPA (7:3) 3 times, the organic was dried and concentrated and used as it. LCMS (m/z): 176.1 (MH+), 0.32 min.

Workup

  1. filtrationfiltered through Celite
  2. extractionThe reaction mixture was then extracted by EtOAc
  3. washwashed 2 times, and water 50 mL once
  4. extractionthe reaction mixture was then extracted by CHCl3/IPA (7:3) 3 times
  5. customthe organic was dried
  6. concentrationconcentrated
  7. custom176.1 (MH+), 0.32 min.

Sources & evidence

ORD record
ord-1b70945a318d41229827085343cd2e37
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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