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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1685179Generated: November 1, 2026

Methyl iodide → 4,6-Dichloro-N-methylpyrimidin-5-amine

https://huagongshe.com/reaction/1685179

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMethyl iodideHCID 6328—
ReactantSodium hydrideHCID 24758—
Reactant5-Amino-4,6-dichloropyrimidineHCID 79434—
SolventTetrahydrofuranHCID 8028—
Product4,6-Dichloro-N-methylpyrimidin-5-amineHCID 25027428.1%

Reaction Conditions

Temperature0 °C

Reaction Steps

Add 5-amino-4,6-dichloropyrimidine (2 g; 0.012 mol) to THF (60 mL). Cool to 0° C. and add portion-wise NaH (0.53 g; 0.013 mol). Stir at 0° C. for 30 min. Add drop-wise methyl iodide (0.7 mL, 0.012 mol). Stir at 0° C. for 1 h and then RT for 30 min. Quench with saturated ammonium chloride aqueous and extract with EA. Evaporate the organic layer and purify the residue through a silica gel column using acetone and hexane as eluent to give the title compound (0.6 g; 27.64%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08148387B2
Source datasetuspto-grants-2012_04
ORD IDord-3d2b197eb1a44b4dae3828aee1d0c42b
Source noteuspto-grants-2012_04