Hydrochloric Acid → 5-(Chloromethyl)-3-methylpyrimidine-2,4(1H,3H)-dione

Reaction equation

[CH3:1][N:2]1[C:7](=[O:8])[C:6]([C:9](O)=O)=[CH:5][NH:4][C:3]1=[O:12].[ClH:13]>>[CH3:1][N:2]1[C:7](=[O:8])[C:6]([CH2:9][Cl:13])=[CH:5][NH:4][C:3]1=[O:12]

Participants

Reactant 2

HCID 313Hydrochloric Acid

HCID 2537713-Methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid

Product 1

HCID 218219955-(Chloromethyl)-3-methylpyrimidine-2,4(1H,3H)-dioneYield 52%

Procedure

3-methyluracil-5-carboxylic acid was treated with HCl and CH2 using standard chloromethylation conditions to give 3-methyl-5-chloromethyl uracil in 52% yield (following standard work-up and recrystallization from ethyl acetate). NMR (DMSO-d6): chemical shifts, peak integrations L D2O exchange experiments diagnostic for structure.

Sources & evidence

ORD record: ord-f8d97e719f024197adad569f1992e044
Source dataset: uspto-grants-2001_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06271195B1

Reaction notes

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