Iodine → 2-chloro-7-iodo-5H-pyrrolo[3,2-d]pyrimidine

HRID 1615591Notes

Reaction equation

HRID 1615591 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[NH:10][CH:9]=[CH:8][C:6]=2[N:7]=1.C(=O)(O)[O-].[Na+].[I-:16].[K+].II>O.[Cl-].[Na+].O>[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[NH:10][CH:9]=[C:8]([I:16])[C:6]=2[N:7]=1

Participants

7

Reactant 4

HCID 807IodineHCID 4875Potassium IodideHCID 516892Sodium BicarbonateHCID 457899862-Chloro-5H-pyrrolo[3,2-d]pyrimidine

Product 1

HCID 455884652-chloro-7-iodo-5H-pyrrolo[3,2-d]pyrimidineYield 83%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

To a suspension of 2-chloro-5H-pyrrolo[3,2-d]pyrimidine (3.55 g, 23.2 mmol) in water (200 ml) was added sodium bicarbonate (19.2 g) A solution of potassium iodide (16.41 g, 98.9 mmol) and iodine (5.78 g, 22.8 mmol) in water (25 ml) was added dropwise then allowed to stir at room temperature for 1 h. The mixture was diluted with brine and extracted with ethyl acetate. The extracts were dried filtered and evaporated. The residue was purified by flash chromatography, eluting with chloroform/methanol 25/1 to 20/1, to afford 2-chloro-7-iodo-5H-pyrrolo[3,2-d]pyrimidine (5.33 g, 83%). 1H NMR (DMSO, 300 MHz): 12.50 (s, 1H), 8.82 (s, 1H), 8.20 (s, 1H); 13C NMR (DMSO, 75 MHz): 143.2, 143.0, 139.7, 139.5, 126.5, 56.2; LRMS (EI): m/z calcd for [M]+ 278.91, 280.91 found 278.95, 280.95.

Workup

  1. additionwas added dropwise
  2. extractionextracted with ethyl acetate
  3. customThe extracts were dried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by flash chromatography
  7. washeluting with chloroform/methanol 25/1 to 20/1

Sources & evidence

ORD record
ord-14475ee857594fcb992dbc895f1220da
Source dataset
uspto-grants-2014_07
Patent number
US08765755B2

Reaction notes

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