Sodium Carbonate → 5-(2-methyl-3,6-dihydro-2H-pyran-4-yl)pyrazin-2-amine

HRID 595840Notes

Reaction equation

HRID 595840 reaction equation
FC(F)(F)S(O[C:7]1[CH2:8][CH:9]([CH3:13])[O:10][CH2:11][CH:12]=1)(=O)=O.CC1(C)C(C)(C)OB([C:24]2[N:25]=[CH:26][C:27]([NH2:30])=[N:28][CH:29]=2)O1.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>[CH3:13][CH:9]1[CH2:8][C:7]([C:24]2[N:25]=[CH:26][C:27]([NH2:30])=[N:28][CH:29]=2)=[CH:12][CH2:11][O:10]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 179989875-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazin-2-amineHCID 1180454962-methyl-3,6-dihydro-2H-pyran-4-yl trifluoromethanesulfonate

Product 1

HCID 1180453955-(2-methyl-3,6-dihydro-2H-pyran-4-yl)pyrazin-2-amineYield 45.4%

Reagents, catalysts & solvents 2

HCID 178418807HCID 178418807, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 2-methyl-3,6-dihydro-2H-pyran-4-yl trifluoromethanesulfonate (0.637 g, 2.88 mmol), 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazin-2-amine (0.914 g, 3.74 mmol), and PdCl2(dppf)-CH2Cl2 adduct (0.235 g, 0.288 mmol) in DME (9.82 mL) was added 2M Na2CO3 (3.27 mL). The reaction mixture was heated at microwave synthesizer (120° C., 10 min). Ethyl acetated was added, and washed with sat NaHCO3, and water. Then the desired compound was extracted to 1N HCl aqueous layer, and washed with EtOAc. Basified with 2N NaOH, and the product was extracted to EtOAc layer. EtOAc organic layer was washed with water and dried over Na2SO4. Filtered and concentrated to provide 250 mg of desired compound. LCMS (m/z): 192.2 (MH+), 0.40 min.

Workup

  1. additionEthyl acetated was added
  2. washwashed
  3. extractionThen the desired compound was extracted to 1N HCl aqueous layer
  4. washwashed with EtOAc
  5. extractionBasified with 2N NaOH, and the product was extracted to EtOAc layer
  6. washEtOAc organic layer was washed with water
  7. dry with materialdried over Na2SO4
  8. filtrationFiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-e82ed1e6ea9e4fdd8a2f4778c27de53b
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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