HCID 178418572, compound → HCID 178418587, compound

HRID 2226010Notes

Reaction equation

HRID 2226010 reaction equation
I[C:2]1[N:3]([I:19])[C:4]([OH:18])=[C:5]2[CH:10]=[C:9]([NH:11][C:12](=[O:17])[C:13]([CH3:16])([CH3:15])[CH3:14])[N:8]=[C:6]2[N:7]=1>C(O)(=O)C.O.[Zn]>[I:19][N:3]1[C:4]([OH:18])=[C:5]2[CH:10]=[C:9]([NH:11][C:12](=[O:17])[C:13]([CH3:15])([CH3:14])[CH3:16])[N:8]=[C:6]2[N:7]=[CH:2]1

Participants

5

Reactant 1

HCID 178418572HCID 178418572, compound

Product 1

HCID 178418587HCID 178418587, compound

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Procedure

To a mixture of 4.86 g of 2,3-diiodo-4-hydroxy-6-pivaloylaminopyrrolo[2,3-d]pyrimidine in 100 mL of glacial acetic acid and 25 mL of water are added 1.3 g (20 mmol) of zinc powder. The mixture is stirred at ambient temperature for 18 hours, diluted with 500 mL of water, and cooled. The solid is collected through filtration and dried under vacuum over phosphorus pentoxide to yield 3-iodo-4-hydroxy-6-pivaloylaminopyrrolo[2,3-d]pyrimidine which can be purified further by chromatography over silica eluting with 2.5% methanol in methylene chloride. mp >240° C. 1NMR (d6 -DMSO)δ1.20(s, 9H), 7.12 (d, J=1.8 Hz, 1 H), 10.82 (s, 1H), 11.79 (s, 1H), 11.89 (s, 1H). Anal. Calc. for C11H13N4O2I: C, 36.69; H 3.64; N, 15.56; I, 35.24. Found: C, 36.91; H, 3.58; N, 15.65; I, 35.56.

Workup

  1. temperaturecooled
  2. filtrationThe solid is collected through filtration
  3. dry with materialdried under vacuum over phosphorus pentoxide

Sources & evidence

ORD record
ord-b7b0646cac784163b4a537768079c2f6
Source dataset
uspto-grants-1994_09
Patent number
US05344932

Reaction notes

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