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

HRID 1354317Notes

Reaction equation

HRID 1354317 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]>>[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

3

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

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% H(aq) (2 ml) at rt was added NaI (206 mg, 1.37 mmol, 5 eq). The reaction mixture stirred at rt 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-dihydrofuro[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-1a20c0ed09f04bcca0119897fbd080a5
Source dataset
uspto-grants-2007_05
Patent number
US07223766B2

Reaction notes

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