Diisopropylethylamine → 6-Bromo-4-(2-(tetrahydro-2H-pyran-4-yl)ethyl)-3,4-dihydropyrazino[2,3-b]pyrazin-2(1H)-one

HRID 1401176Notes

Reaction equation

HRID 1401176 reaction equation
Br[CH2:2][C:3]([NH:5][C:6]1[C:11](Br)=[N:10][C:9]([Br:13])=[CH:8][N:7]=1)=[O:4].Cl.[O:15]1[CH2:20][CH2:19][CH:18]([CH2:21][CH2:22][NH2:23])[CH2:17][CH2:16]1.C(N(C(C)C)CC)(C)C>>[Br:13][C:9]1[N:10]=[C:11]2[N:23]([CH2:22][CH2:21][CH:18]3[CH2:19][CH2:20][O:15][CH2:16][CH2:17]3)[CH2:2][C:3](=[O:4])[NH:5][C:6]2=[N:7][CH:8]=1

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 441186952-(Oxan-4-yl)ethan-1-amine hydrochlorideHCID 582983072-bromo-N-(3,5-dibromopyrazin-2-yl)acetamide

Product 1

HCID 715670836-Bromo-4-(2-(tetrahydro-2H-pyran-4-yl)ethyl)-3,4-dihydropyrazino[2,3-b]pyrazin-2(1H)-oneYield 50.7%

Conditions

Temperature
85 °C

Procedure

2-Bromo-N-(3,5-dibromopyrazin-2-yl)acetamide (3.30 g, 8.83 mmol) and 2-(tetrahydro-2H-pyran-4-yl)ethanamine hydrochloride (1.46, 8.83 mmol) and diisopropyl ethylamine (6.67 mL, 35.3 mmol) were combined and heated at 85° C. Upon complete consumption of starting material (by TLC), the reaction solution was condensed and purified via Biotage chromatography (0-100% ethyl acetate in hexanes) to afford the title compound (1.53 g, 4.48 mmol, 50% yield). MS (ESI) m/z 341.4 [M]+, 343.1 [M+2]+.

Workup

  1. customUpon complete consumption of starting material (by TLC)
  2. customcondensed
  3. custompurified via Biotage chromatography (0-100% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-aa225e20f41c47c6aaf4c5ff6855943a
Source dataset
uspto-grants-2014_12
Patent number
US08907087B2

Reaction notes

Loading…