Allyl bromide → HCID 178460812, compound

HRID 1405985Notes

Reaction equation

HRID 1405985 reaction equation
[F:1][C:2]1[C:3](=[S:9])[NH:4][C:5](=[O:8])[NH:6][CH:7]=1.C[O-].[Na+].[CH2:13](Br)[CH:14]=[CH2:15]>CO>[CH2:15]([S:9][C:3]1[C:2]([F:1])=[CH:7][NH:6][C:5](=[O:8])[N:4]=1)[CH:14]=[CH2:13]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 27812135-Fluoro-4-thiouracilHCID 10942334Sodium Methoxide

Product 1

HCID 178460812HCID 178460812, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

This material was prepared by the procedure described in Tetrahedron 1985, 41, 5289-5293. To a solution of 5-fluoro-4-thioxo-3,4-dihydropyrimidin-2(1H)-one (12.4 g, 84.9 mmol) and sodium methoxide (4.54 g, 84.9 mmol) in MeOH (100 mL) was added dropwise allyl bromide (10.27 g, 84.9 mmol) at room temperature. The reaction mixture was stirred overnight at room temperature. After removal of solvent, the residue was purified by normal phase chromatography (gradient, 10 to 33% EtOAc/hexane), to give 4-(allylthio)-5-fluoropyrimidin-2(1H)-one (6 g, 38%) as a white solid: mp 150-152° C.; 1H NMR (301 MHz, DMSO-d6) δ 11.60 (s, 1H), 8.00 (d, J=4.5 Hz, 1H), 5.90 (ddt, J=16.8, 10.0, 6.8 Hz, 1H), 5.34 (dd, J=16.9, 1.4 Hz, 1H), 5.15 (dd, J=10.0, 0.7 Hz, 1H), 3.83 (d, J=6.8 Hz, 2H); ESIMS m/z 187 ([M+H]+).

Workup

  1. customThis material was prepared by the procedure
  2. customAfter removal of solvent
  3. customthe residue was purified by normal phase chromatography (gradient, 10 to 33% EtOAc/hexane)

Sources & evidence

ORD record
ord-2e3b234f7e0c48749e0a7bd3228abfb7
Source dataset
uspto-grants-2014_12
Patent number
US08916579B2

Reaction notes

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