Tetrahydrofuran → HCID 117653359, compound

HRID 2200319Notes

Reaction equation

HRID 2200319 reaction equation
[CH2:1]([N:3]1[C:8]2=[N:9][C:10](B3OC(C)(C)C(C)(C)O3)=[CH:11][N:12]=[C:7]2[NH:6][CH2:5][C:4]1=[O:22])[CH3:2].Br[C:24]1[C:25]([CH3:41])=[N:26][C:27]([C:30]2[N:34]=[CH:33][N:32]([CH:35]3[CH2:40][CH2:39][CH2:38][CH2:37][O:36]3)[N:31]=2)=[CH:28][CH:29]=1.C(=O)([O-])O.[K+].O1CCCC1>Cl[Pd]Cl.O>[CH2:1]([N:3]1[C:8]2=[N:9][C:10]([C:24]3[C:25]([CH3:41])=[N:26][C:27]([C:30]4[N:34]=[CH:33][N:32]([CH:35]5[CH2:40][CH2:39][CH2:38][CH2:37][O:36]5)[N:31]=4)=[CH:28][CH:29]=3)=[CH:11][N:12]=[C:7]2[NH:6][CH2:5][C:4]1=[O:22])[CH3:2]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 516893Potassium BicarbonateHCID 582983093-bromo-2-methyl-6-(1-(tetrahydro-2H-pyran-2-yl)-1H-1,2,4-triazol-3-yl)pyridineHCID 67153814HCID 67153814, compound

Product 1

HCID 117653359HCID 117653359, compound

Reagents, catalysts & solvents 2

HCID 24290Palladium ChlorideCatalystHCID 962WaterSolvent

Conditions

Temperature
55 °C

Procedure

A portion of 1-ethyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydropyrazino[2,3-b]pyrazin-2(1H)-one (1 equiv), 3-bromo-2-methyl-6-(1-(tetrahydro-2H-pyran-2-yl)-1H-1,2,4-triazol-3-yl)pyridine (0.95 equiv), potassium hydrogen carbonate (2.3 equiv), and PdCl2 Amphos2 (0.001 equiv) were treated with a mixture of tetrahydrofuran and water, and the reaction mixture was heated to 55° C. The reaction mixture was cooled and the organic layer was treated with activated carbon at ambient temperature and filtered. The filtrate was distilled to 70% of its original volume, cooled, treated with water, seeded, and treated with additional water. The solids were filtered and washed with tetrahydrofuran/water and dried to obtain 1-ethyl-7-(2-methyl-6-(1-(tetrahydro-2H-pyran-2-yl)-1H-1,2,4-triazol-3-yl)pyridin-3-yl)-3,4-dihydropyrazino[2,3-b]pyrazin-2(1H)-one as a solid.

Workup

  1. temperatureThe reaction mixture was cooled
  2. additionthe organic layer was treated with activated carbon at ambient temperature
  3. filtrationfiltered
  4. distillationThe filtrate was distilled to 70% of its original volume
  5. temperaturecooled
  6. additiontreated with water
  7. additiontreated with additional water
  8. filtrationThe solids were filtered
  9. washwashed with tetrahydrofuran/water
  10. customdried

Sources & evidence

ORD record
ord-4880c01b8f6e4b22b533dc104de04750
Source dataset
uspto-grants-2016_06
Patent number
US09359364B2

Reaction notes

Loading…