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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 227579Generated: October 26, 2026

Methyl iodide → 5-(1,1-Dimethylethyl) 4-methyl 6-methyl-4,5-pyrimidinedicarboxylate

https://huagongshe.com/reaction/227579

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMethyl iodideHCID 6328—
ReactantLithium CarbonateHCID 11125—
Reactant5-(1,1-Dimethylethyl) hydrogen 6-methyl-4,5-pyrimidinedicarboxylateHCID 67182510—
SolventDimethylformamideHCID 6228—
Product5-(1,1-Dimethylethyl) 4-methyl 6-methyl-4,5-pyrimidinedicarboxylateHCID 6718433679.1%

Reaction Conditions

Temperature60 °C

Reaction Steps

To a solution of 9.12 g (38 mmol) of the material from Step B in 100 mL of N,N-dimethyl formamide (DMF) was added 3.1 mL (50 mmol) of iodomethane and 3.7 g (50 mmol) of lithium carbonate. The reaction mixture was heated at 60° C. for 3 hours. After cooling the reaction mixture was partitioned between dichloromethane and water. The organic layer was dried (sodium sulfate) and the solvent was removed with a rotary evaporator and then a vacuum pump. The residue was purified by MPLC with a gradient of 20-30% ethyl acetate in hexanes as eluant to afford 7.58 g of the title compound as an off-white solid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07560564B2
Source datasetuspto-grants-2009_07
ORD IDord-945412e5f1a24566adb2db44b9eadcf2
Source noteuspto-grants-2009_07