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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1676341Generated: October 30, 2026

Dimethylformamide → Methyl 4-(cyclopropylmethyl)-3-oxo-3,4-dihydropyrazine-2-carboxylate

https://huagongshe.com/reaction/1676341

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethylformamideHCID 6228—
ReactantLithium hydrideHCID 62714—
ReactantBromomethylcyclopropaneHCID 81503—
ReactantMethyl 2-oxo-1,2-dihydropyridine-3-carboxylateHCID 579028—
SolventEthyl AcetateHCID 8857—
ProductMethyl 4-(cyclopropylmethyl)-3-oxo-3,4-dihydropyrazine-2-carboxylateHCID 6734967564%

Reaction Conditions

Temperature50 °C

Reaction Steps

LiH (7.7 mg, 0.97 mmol) was added to the solution of methyl 2-oxo-1,2-dihydropyridine-3-carboxylate (0.10 g, 0.65 mmol) in DMF (3 mL) at 0° C. After stirring for 30 minutes, (bromomethyl) cyclopropane (0.18 g, 1.30 mmol) was added to the reaction mixture at the temperature, and the reaction was warmed to 50° C. After stirring for 3 days at 50° C., the reaction mixture was diluted with EtOAc, quenched with ice water, extracted with EtOAc, dried over MgSO4, and concentrated. The crude was purified by silica gel flash column chromatography (2% MeOH in CH2Cl2) to afford 87 mg (64%) of the desired product.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08003662B2
Source datasetuspto-grants-2011_08
ORD IDord-ea47cddff03044db918ed97dd2b039c8
Source noteuspto-grants-2011_08