tert-Butyl methyl ether → Methyl 2-chloro-6-(1-ethoxyvinyl)pyrimidine-4-carboxylate

HRID 59113

Reaction equation

[Cl:1][C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[C:4](Cl)[N:3]=1.C([Sn](CCCC)(CCCC)[C:18]([O:20][CH2:21][CH3:22])=[CH2:19])CCC.[F-].[K+].CC(OC)(C)C>CN(C=O)C.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:1][C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[C:4]([C:18]([O:20][CH2:21][CH3:22])=[CH2:19])[N:3]=1

Participants

Conditions

Temperature: 94 °C

Procedure

Methyl 2,6-dichloropyrimidine-4-carboxylate (8.44 g, 40.77 mmol) and bis(triphenylphosphine)-palladium(II) chloride (0.572 g, 0.82 mmol) in DMF (80 mL) was degased. Tributyl(1-ethoxy-vinyl)tin (14.46 mL, 42.81 mmol) was added under argon. The mixture was heated at 94° C. for 1 h. The mixture was poured into a solution of potassium fluoride (30 g) in water (400 mL). MTBE (300 mL) was added and the mixture was stirred for 10 min. The mixture was filtered and the filter was washed with 200 mL of MTBE. The filtrate was washed with brine (100 mL), dried over sodium sulfate and the solvents were evaporated. The residue purified by column chromatography on silica eluting with DCM to give the title compound as a solid (7.40 g, 75%).

Workup

filtrationThe mixture was filtered
washthe filter was washed with 200 mL of MTBE
washThe filtrate was washed with brine (100 mL)
dry with materialdried over sodium sulfate
customthe solvents were evaporated
customThe residue purified by column chromatography on silica eluting with DCM

Sources & evidence

ORD record: ord-04fc7098ba644efc9570b0c89b16e660
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09439904B2

Linked notes

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