2-Methoxyethylamine → 7-Bromo-1-(2-methoxyethyl)-3,4-dihydropyrazino[2,3-b]pyrazin-2(1H)-one

HRID 717179Notes

Reaction equation

Br[C:2]1[C:3]([NH:9][CH2:10][C:11]([O:13]CC)=O)=[N:4][CH:5]=[C:6]([Br:8])[N:7]=1.[CH3:16][O:17][CH2:18][CH2:19][NH2:20].C(N(C(C)C)CC)(C)C.C(OCC)(=O)C.O>CS(C)=O.C(O)(=O)C>[Br:8][C:6]1[N:7]=[C:2]2[N:20]([CH2:19][CH2:18][O:17][CH3:16])[C:11](=[O:13])[CH2:10][NH:9][C:3]2=[N:4][CH:5]=1

Participants

Conditions

Temperature: 150 °C

Procedure

Ethyl 2-(3,5-dibromopyrazin-2-ylamino)acetate (See Example 1.C) (1 equiv), 2-methoxyethanamine (1 equiv), diisopropylethylamine (3 equiv), were suspended in dimethylsulfoxide and heated in an Emrys Biotage microwave reactor at 150° C. for 1 h. Standard ethyl acetate/water work up gave crude material, which was suspended in 99.7% acetic acid. The reaction was sealed, heated to 120° C. and allowed to stir for 2 h. The reaction was extracted in ethyl acetate. The organic layers were pooled and washed with saturated sodium bicarbonate, followed by brine and dried over magnesium sulfate. Concentration and flash column chromatography (0-100% ethyl acetate in hexanes) gave the desired product in 27% yield over two steps. MS (ESI) m/z 287.4 [M]+, 289.4 [M+2]+.

Workup

customThe reaction was sealed
temperatureheated to 120° C.
extractionThe reaction was extracted in ethyl acetate
washwashed with saturated sodium bicarbonate
dry with materialdried over magnesium sulfate
concentrationConcentration and flash column chromatography (0-100% ethyl acetate in hexanes)

Sources & evidence

ORD record: ord-88c89689729749a196d4b599f47146d0
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193692B2

Reaction notes

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