Diisopropylethylamine → 3-Bromo-N-[2-(morpholin-4-yl)ethyl]imidazo[1,2-a]pyrazin-8-amine

HRID 457012Notes

Reaction equation

[Br:1][C:2]1[N:6]2[C:7](Br)=[CH:8][N:9]=[CH:10][C:5]2=[N:4][CH:3]=1.[N:12]1([CH2:18][CH2:19][NH2:20])[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1.C(N(C(C)C)CC)(C)C>CO.C(Cl)Cl.O>[Br:1][C:2]1[N:6]2[CH:7]=[CH:8][N:9]=[C:10]([NH:20][CH2:19][CH2:18][N:12]3[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)[C:5]2=[N:4][CH:3]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of 3,5-dibromo-imidazo[1,2-a]pyrazine (D) (200 mg, 0.72 mmol) in methanol (3.6 ml) was added (2-morpholin-4-yl-ethyl)-amine (2.5 eq.) and diisopropylethylamine (DIPEA) (0.383 ml, 4.5 mmol). The mixture was heated at 70° C. overnight. The mixture was then cooled to rt, diluted with DCM and water. The organic layer was washed with brine, dried and concentrated. The residue was purified on a silica gel column to give 34 mg (yield 14%) of the title compound.

Workup

temperatureThe mixture was then cooled to rt
washThe organic layer was washed with brine
customdried
concentrationconcentrated
customThe residue was purified on a silica gel column

Sources & evidence

ORD record: ord-f14bd7942eed40f99bb80828777d6eb6
Source dataset: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07186832B2

Reaction notes

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