Sodium Carbonate → HCID 118045520, compound

HRID 595892Notes

Reaction equation

HRID 595892 reaction equation
Br[C:2]1[N:3]=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=1.[CH2:9]([O:11]/[CH:12]=[CH:13]/B1OC(C)(C)C(C)(C)O1)[CH3:10].C([O-])([O-])=O.[Na+].[Na+]>COCCOC.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>[CH2:12]([O:11]/[CH:9]=[CH:10]/[C:2]1[N:3]=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=1)[CH3:13]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 5995392-Amino-5-bromopyrazineHCID 219739081-Ethoxyethene-2-boronic acid pinacol ester

Product 1

HCID 118045520HCID 118045520, compound

Reagents, catalysts & solvents 2

HCID 178418807HCID 178418807, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
130 °C

Procedure

To a solution of 5-bromopyrazin-2-amine (200 mg, 1.149 mmol) in DME (2874 μL) was added (E)-2-(2-ethoxyvinyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (341 mg, 1.724 mmol), PdCl2(dppf)-CH2Cl2 adduct (94 mg, 0.115 mmol), and 2M Na2CO3 (958 μL). The reaction mixture was stirred at 130° C. in microwave reactor for 20 min. The reaction mixture was filtered through Celite and washed with EtOAc, the filtrate was partition between EtOAc and water. The aqueous was extracted by EtOAc three times, the combined organic was dried and concentrated. The crude material was purified by flash chromatography to give (E)-5-(2-ethoxyvinyl)pyrazin-2-amine. LCMS (m/z): 166.1 (MH+), 0.41 min.

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. washwashed with EtOAc
  3. customthe filtrate was partition between EtOAc and water
  4. extractionThe aqueous was extracted by EtOAc three times
  5. customthe combined organic was dried
  6. concentrationconcentrated
  7. customThe crude material was purified by flash chromatography

Sources & evidence

ORD record
ord-638fdf8f7bb84d9e99b1c4584950439b
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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