Ethyl 2-(5-bromo-3-((tetrahydro-2H-pyran-4-yl)methylamino)pyrazin-2-ylamino)acetate → 7-bromo-1-((tetrahydro-2H-pyran-4-yl)methyl)-3,4-dihydropyrazino[2,3-b]pyrazin-2(1H)-one

HRID 717118Notes

Reaction equation

HRID 717118 reaction equation
[Br:1][C:2]1[N:3]=[C:4]([NH:15][CH2:16][CH:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)[C:5]([NH:8][CH2:9][C:10](OCC)=[O:11])=[N:6][CH:7]=1>C(O)(=O)C>[Br:1][C:2]1[N:3]=[C:4]2[N:15]([CH2:16][CH:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)[C:10](=[O:11])[CH2:9][NH:8][C:5]2=[N:6][CH:7]=1

Participants

3

Reactant 1

HCID 86644641Ethyl 2-(5-bromo-3-((tetrahydro-2H-pyran-4-yl)methylamino)pyrazin-2-ylamino)acetate

Product 1

HCID 866446427-bromo-1-((tetrahydro-2H-pyran-4-yl)methyl)-3,4-dihydropyrazino[2,3-b]pyrazin-2(1H)-oneYield 68.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A stirred solution of ethyl 2-(5-bromo-3-((tetrahydro-2H-pyran-4-yl)methylamino)pyrazin-2-ylamino)acetate (1.474 g, 3.95 mmol) in acetic acid (13 mL) in a sealed vessel was heated at 120° C. in an oil bath for 2 h. The acetic acid was removed under reduced pressure. The residue was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate, shaken and the layers separated. The water layer was extracted twice with ethyl acetate. The combined organics were dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was taken up in dichloromethane and hexane and the resulting solids collected by vacuum filtration. The solids were washed with hexane and dried under vacuum to give the desired product (0.879 g, 2.688 mmol, 68% yield) as a purple solid. MS (ESI) m/z 327.1 [M]+, 329.0 [M+2]+.

Workup

  1. customThe acetic acid was removed under reduced pressure
  2. customThe residue was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate
  3. customthe layers separated
  4. extractionThe water layer was extracted twice with ethyl acetate
  5. dry with materialThe combined organics were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. filtrationhexane and the resulting solids collected by vacuum filtration
  9. washThe solids were washed with hexane
  10. customdried under vacuum

Sources & evidence

ORD record
ord-7644abf8e6694744bc73cf245800cfba
Source dataset
uspto-grants-2015_11
Patent number
US09193692B2

Reaction notes

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