Sodium Iodide → 2-(5-Chloro-2-fluorophenyl)-4-iodo-5,7-dihydrofuro[3,4-d]pyrimidine

HRID 1010850Notes

Reaction equation

HRID 1010850 reaction equation
Cl[C:2]1[C:3]2[CH2:18][O:17][CH2:16][C:4]=2[N:5]=[C:6]([C:8]2[CH:13]=[C:12]([Cl:14])[CH:11]=[CH:10][C:9]=2[F:15])[N:7]=1.[Na+].[I-:20]>I>[Cl:14][C:12]1[CH:11]=[CH:10][C:9]([F:15])=[C:8]([C:6]2[N:7]=[C:2]([I:20])[C:3]3[CH2:18][O:17][CH2:16][C:4]=3[N:5]=2)[CH:13]=1

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 211043384-Chloro-2-(5-chloro-2-fluorophenyl)-5,7-dihydrofuro[3,4-d]pyrimidine

Product 1

HCID 211043072-(5-Chloro-2-fluorophenyl)-4-iodo-5,7-dihydrofuro[3,4-d]pyrimidine

Reagents, catalysts & solvents 1

HCID 24841Hydrogen iodideSolvent

Procedure

To a suspension of 4-chloro-2-(5-chloro-2-fluorophenyl)-5,7-dihydrofuro[3,4-d]-pyrimidine (78 mg, 0.275 mmol, 1 eq) in 57% HI(aq) (2 ml) at r.t. was added NaI (206 mg, 1.37 mmol, 5 eq). The reaction mixture was stirred at r.t. overnight and then was poured onto ice. The product was extracted with chloroform and the aqueous layer was neutralized with NaHCO3 and extracted further with chloroform. The organic layers were combined washed with brine, dried (MgSO4), filtered and evaporated in vacuo to provide a crude residue of 2-(5-Chloro-2-fluorophenyl)-4-iodo-5,7-dihydro-furo[3,4-d]pyrimidine which was not further purified.

Workup

  1. additionwas poured onto ice
  2. extractionThe product was extracted with chloroform
  3. extractionextracted further with chloroform
  4. washThe organic layers were combined washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-de5da2df8699439a845c7a1507fc159f
Source dataset
uspto-grants-2011_07
Patent number
US07977342B2

Reaction notes

Loading…