Sodium Iodide → 2-(5-Chloro-2-fluorophenyl)-4-iodo-6,7-dihydrofuro[3,2-d]pyrimidine

HRID 1010862Notes

Reaction equation

HRID 1010862 reaction equation
Cl[C:2]1[C:3]2[O:18][CH2:17][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.[IH:19].[Na+].[I-]>O>[Cl:14][C:12]1[CH:11]=[CH:10][C:9]([F:15])=[C:8]([C:6]2[N:7]=[C:2]([I:19])[C:3]3[O:18][CH2:17][CH2:16][C:4]=3[N:5]=2)[CH:13]=1

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 24841Hydrogen iodideHCID 211043394-Chloro-2-(5-chloro-2-fluorophenyl)-6,7-dihydrofuro[3,2-d]pyrimidine

Product 1

HCID 211043102-(5-Chloro-2-fluorophenyl)-4-iodo-6,7-dihydrofuro[3,2-d]pyrimidine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of 4-chloro-2-(5-chloro-2-fluorophenyl)-6,7-dihydrofuro[3,2-d]-pyrimidine (80 mg, 0.28 mmol, 1 eq) in a 57% HI solution in water (2 ml) at rt. was added NaI (206 mg, 1.41 mmol, 5 eq). The reaction mixture was stirred at r.t. overnight and then poured onto ice. The product was extracted with chloroform and the aqueous layer was neutralized with NaHCO3 and extracted further with more chloroform. The organic layers were combined washed with brine, dried (MgSO4), filtered and evaporated in vacuo to provide a crude residue 2-(5-chloro-2-fluorophenyl)-4-iodo-6,7-dihydrofuro[3,2-d]pyrimidine that was not further purified.

Workup

  1. additionpoured onto ice
  2. extractionThe product was extracted with chloroform
  3. extractionextracted further with more 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-2ab9d39d2cc14e988bf03f47dbbee841
Source dataset
uspto-grants-2011_07
Patent number
US07977342B2

Reaction notes

Loading…