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

HRID 227579

Reaction equation

[CH3:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([C:8]([OH:10])=[O:9])[C:3]=1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12].IC.[C:20](=O)([O-])[O-].[Li+].[Li+]>CN(C)C=O>[CH3:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([C:8]([O:10][CH3:20])=[O:9])[C:3]=1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12]

Participants

Conditions

Temperature: 60 °C

Procedure

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.

Workup

temperatureAfter cooling the reaction mixture
customwas partitioned between dichloromethane and water
dry with materialThe organic layer was dried (sodium sulfate)
customthe solvent was removed with a rotary evaporator
customThe residue was purified by MPLC with a gradient of 20-30% ethyl acetate in hexanes as eluant

Sources & evidence

ORD record: ord-945412e5f1a24566adb2db44b9eadcf2
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07560564B2

Linked notes

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