Hydrochloric Acid → 7-Bromo-1-(2-(tetrahydro-2H-pyran-4-yl)ethyl)-3,4-dihydropyrazino[2,3-b]pyrazin-2(1H)-one

HRID 1047272Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

Ethyl 2-(5-bromo-3-(2-(tetrahydro-2H-pyran-4-yl)ethylamino)pyrazin-2-ylamino)acetate (0.5 g, 1.291 mmol) and hydrochloric acid (6 M in water, 0.215 mL, 1.291 mmol) were combined in ethanol (2 mL) and the resulting mixture was heated in a Biotage Emrys Optimizer microwave reactor at 100° C. for 2400 s. The reaction mixture was concentrated and purified using silica gel chromatography (33% ethyl acetate in hexanes) to yield the title compound (quantitative yield). MS (ESI) m/z 341.1 [M]+, 343.1 [M+2]+.

Workup

concentrationThe reaction mixture was concentrated
custompurified

Sources & evidence

ORD record: ord-24dfefafab614c09bc5985f03debce50
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08569494B2

Reaction notes

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