Hydrochloric Acid → HCID 58443073, compound

HRID 1038970Notes

Reaction equation

HRID 1038970 reaction equation
[H-].[Na+].[O:3]=[C:4]1[NH:9][CH:8]=[N:7][CH:6]=[C:5]1[C:10]([O:12][CH2:13][CH3:14])=[O:11].[F:15][C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][C:23]=1[F:24])[CH2:19]Br.Cl>CN(C=O)C>[F:15][C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][C:23]=1[F:24])[CH2:19][N:9]1[C:4](=[O:3])[C:5]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:6][N:7]=[CH:8]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 963476-Oxo-1,6-dihydro-pyrimidine-5-carboxylic acid ethyl esterHCID 5814364-(Bromomethyl)-1,2-difluorobenzene

Product 1

HCID 58443073HCID 58443073, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of sodium hydride (0.262 g, 6.54 mmol, 60% dispersion in mineral oil) and ethyl 6-oxo-1,6-dihydropyrimidine-5-carboxylate (1 g, 5.95 mmol) was dissolved in DMF (11.89 ml). After 30 min at room temperature, 3,4-difluorobenzyl bromide (0.761 ml, 5.95 mmol) was added. The reaction mixture was stirred at room temperature overnight and then poured into aqueous hydrochloric acid (10%). The aqueous layer was extracted with ethyl acetate. The combined organic extracts were washed with brine, dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel, eluting with ethyl acetate/hexanes, to afford ethyl 1-(3,4-difluorobenzyl)-6-oxo-1,6-dihydropyrimidine-5-carboxylate as an off-white solid. LRMS (EST) calc'd for (C14H13F2N2O3) [M+H]+, 295.1; found 295.1.

Workup

  1. extractionThe aqueous layer was extracted with ethyl acetate
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel
  6. washeluting with ethyl acetate/hexanes

Sources & evidence

ORD record
ord-5af24e96ab9d48f8b1ba78f6d0953e9f
Source dataset
uspto-grants-2013_10
Patent number
US08552019B2

Reaction notes

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