Iodine → HCID 58994166, compound

HRID 12650Notes

Reaction equation

HRID 12650 reaction equation
[F:1][C:2]1[C:3]([O:13][Si](C)(C)C)=[N:4][C:5]([O:8][Si](C)(C)C)=[N:6][CH:7]=1.Br[CH2:19][CH2:20][CH2:21][Cl:22].II.[OH-].[Na+]>ClCCCl.O>[Cl:22][CH2:21][CH2:20][CH2:19][N:6]1[CH:7]=[C:2]([F:1])[C:3](=[O:13])[NH:4][C:5]1=[O:8]

Participants

7

Reactant 4

HCID 807IodineHCID 80061-Bromo-3-chloropropaneHCID 14798Sodium HydroxideHCID 140203O,O'-Bis(trimethylsilyl)-5-fluorouracil

Product 1

HCID 58994166HCID 58994166, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 962WaterSolvent

Procedure

A mixture of 5-fluoro-2,4-bis[(trimethylsilyl)oxy]pyrimidine (1 g, commercially available from Lancaster), 1-bromo-3-chloropropane (0.44 mL) and I2 (10 mg) in 1,2-dichloroethane (10 mL) was heated to reflux for 30 h. Then the reaction mixture was treated with water and the pH was brought to 7 using aqueous 6N NaOH solution, the mixture was extracted twice with DCM, the organic phase dried over Na2SO4 and the solvent evaporated under reduced pressure. The crude product was purified by flash chromatography on silica gel eluting with DCM/MeOH 95/5 to give 35 mg of the title compound.

Workup

  1. temperatureto reflux for 30 h
  2. extractionthe mixture was extracted twice with DCM
  3. dry with materialthe organic phase dried over Na2SO4
  4. customthe solvent evaporated under reduced pressure
  5. customThe crude product was purified by flash chromatography on silica gel eluting with DCM/MeOH 95/5

Sources & evidence

ORD record
ord-0f56a0657d244ad79378abcbc156cbfa
Source dataset
uspto-grants-2010_06
Patent number
US07727988B2

Reaction notes

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