Ethyl bromopyruvate → Ethyl 8-morpholinoimidazo[1,2-a]pyrazine-2-carboxylate

HRID 1772585Notes

Reaction equation

[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[C:8]([NH2:13])=[N:9][CH:10]=[CH:11][N:12]=2)[CH2:3][CH2:2]1.Br[CH2:15][C:16](=O)[C:17]([O:19][CH2:20][CH3:21])=[O:18]>CN(C=O)C>[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[C:8]3[N:9]([CH:15]=[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[N:13]=3)[CH:10]=[CH:11][N:12]=2)[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of compound 1b (6.00 g, 33.3 mmol) in DMF (100 mL) was added ethyl 3-bromo-2-oxopropanoate (8.00 g, 41.0 mmol) dropwise with stirring. The resulting solution was stirred at rt overnight. The reaction mixture was cooled to 0° C. The solids were collected by filtration and washed with Et2O (3×100 mL). Compound 1c was obtained as a white solid (8.40 g, 81% yield). Mass Spectrum (LCMS, ESI pos.): Calcd. for C13H16N4O3: 276.1 (M+H). found: 276.3.

Workup

stirringThe resulting solution was stirred at rt overnight
filtrationThe solids were collected by filtration
washwashed with Et2O (3×100 mL)

Sources & evidence

ORD record: ord-ff5fdcc8ff4b45fdb76f949eddecca7d
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09249163B2

Reaction notes

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