2-(Oxan-4-yl)ethan-1-amine → 7-(1H-Pyrrolo[2,3-b]pyridin-5-yl)-1-(2-(tetrahydro-2h-pyran-4-yl)ethyl)-3,4-dihydropyrazino[2,3-b]pyrazin-2(1H)-one

HRID 454343Notes

Reaction equation

HRID 454343 reaction equation
Br[C:2]1[N:3]=[C:4]([NH:15][CH2:16][CH2:17][CH:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)[C:5]([NH:8][CH2:9][C:10]([O:12]CC)=O)=[N:6][CH:7]=1.Br[C:25]1[C:26]([NH:32][CH2:33][C:34](OCC)=O)=[N:27][CH:28]=[C:29](Br)N=1.O1CCC(CCN)C[CH2:40]1>CS(C)=O>[NH:27]1[C:26]2=[N:32][CH:33]=[C:34]([C:2]3[N:3]=[C:4]4[N:15]([CH2:16][CH2:17][CH:18]5[CH2:19][CH2:20][O:21][CH2:22][CH2:23]5)[C:10](=[O:12])[CH2:9][NH:8][C:5]4=[N:6][CH:7]=3)[CH:40]=[C:25]2[CH:29]=[CH:28]1

Participants

5

Reactant 3

HCID 27731982-(Oxan-4-yl)ethan-1-amineHCID 57550751Ethyl 2-(3,5-dibromopyrazin-2-ylamino)acetateHCID 86644650Ethyl 2-(5-bromo-3-(2-(tetrahydro-2H-pyran-4-yl)ethylamino)pyrazin-2-ylamino)acetate

Product 1

HCID 594530677-(1H-Pyrrolo[2,3-b]pyridin-5-yl)-1-(2-(tetrahydro-2h-pyran-4-yl)ethyl)-3,4-dihydropyrazino[2,3-b]pyrazin-2(1H)-oneYield 44%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
150 °C

Procedure

Ethyl 2-(5-bromo-3-(2-(tetrahydro-2H-pyran-4-yl)ethylamino)pyrazin-2-ylamino)acetate. Ethyl 2-(3,5-dibromopyrazin-2-ylamino)acetate (See Example 6.B) (1.0 g, 2.95 mmol) and 2-(tetrahydro-2H-pyran-4-yl)ethanamine (0.381 g, 2.95 mmol) were placed in a microwave via, dimethylsulfoxide (2 mL) was added and the resulting mixture was heated in a Biotage Emrys Optimizer microwave reactor at 150° C. for 3600 s. The crude reaction mixture was purified using silica gel chromatography (33% ethyl acetate in hexanes) to yield the title compound (0.5 g, 1.3 mmol, 44% yield). MS (ESI) m/z 387.1 [M]+, 389.1 [M+2]+.

Workup

  1. additionwas added
  2. customThe crude reaction mixture
  3. customwas purified

Sources & evidence

ORD record
ord-e5db7d76d0194828bf1df2eef50dbd00
Source dataset
uspto-grants-2013_07
Patent number
US08492381B2

Reaction notes

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