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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2170319Generated: October 25, 2026

Water → 5-Bromo-2-(methylthio)pyrimidine-4-carbaldehyde

https://huagongshe.com/reaction/2170319

Reaction equation

Participants

RoleNameHCIDCharge
ReactantWaterHCID 962—
ReactantSodium HydroxideHCID 14798—
ReactantAluminium lithium hydrideHCID 21226445—
Reactant5-bromo-N-methoxy-N-methyl-2-(methylthio)pyrimidine-4-carboxamideHCID 90280334—
SolventTetrahydrofuranHCID 8028—
Product5-Bromo-2-(methylthio)pyrimidine-4-carbaldehydeHCID 54271495—

Reaction Steps

A solution of 5-bromo-N-methoxy-N-methyl-2-(methylthio)pyrimidine-4-carboxamide (11A, 8.2 g, 28 mmol) in THF (120 mL) was added dropwise to a suspension of lithium aluminum hydride (1.06 G, 28 mmol) and THF (120 mL) at −78° C. The mixture was stirred for 10 minutes after addition finish. H2O (1.06 mL), 15% aqueous NaOH solution (1.06 mL) and H2O (3.18 mL) were successively added to the mixture at 0° C. very slowly. The resulting precipitate was filtered and washed with THF. The filtrate was concentrated in vacuo to afford crude of the title compound. MS (m/z): 233.14, [M+H]+.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09050344B2
Source datasetuspto-grants-2015_06
ORD IDord-56e05154f5b4483a8c1a60f055d18f8e
Source noteuspto-grants-2015_06