N-Iodosuccinimide → HCID 178478354, compound

HRID 57783Notes

Reaction equation

HRID 57783 reaction equation
[Cl:1][C:2]1[NH:7][C:6]2=[CH:8][CH:9]=[N:10][C:5]2=[C:4]([Cl:11])[N:3]=1.C1C(=O)N([I:19])C(=O)C1>C1COCC1>[I:19][C:8]1[CH:9]=[N:10][C:5]2[C:6]=1[NH:7][C:2]([Cl:1])=[N:3][C:4]=2[Cl:11]

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 178478353HCID 178478353, compound

Product 1

HCID 178478354HCID 178478354, compoundYield 54.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2,4-dichloro pyrrolo[3,2-d]pyrimidine 19 (100 mg, 0.53 mmol) in anhydrous THF (5 mL), NIS (144 mg, 0.64 mmol) was added under N2 atmosphere and stirred for 2 h after which TLC indicated consumption of 19. The solvent was removed in vacuo and the residue dissolved in EtOAc. The organic phase was washed with aq. solution of Na2S2O3 followed by water, brine and then dried over MgSO4. The organic layer was concentrated in vacuo and loaded on silica. The product 20 was purified using column chromatography eluting with 9:1 hexanes/EtOAc to obtain product as off-white solid (90 mg, 54%). Rf 0.55 in 3:1 hexanes/EtOAc. Mp decomposed from 160-230° C. 1H NMR (400 MHz, DMSO-d6): δ 8.29 (s, 1H), 13.19 (s, 1H, NH). 13C NMR (400 MHz, DMSO-d6): δ 58.2, 124.4, 140.9, 143.5, 149.8, 153.5. ESI-MS m/z for calculated [M+H]+ 313.8743. found 313.8740.

Workup

  1. customconsumption of 19
  2. customThe solvent was removed in vacuo
  3. dissolutionthe residue dissolved in EtOAc
  4. washThe organic phase was washed with aq. solution of Na2S2O3
  5. dry with materialdried over MgSO4
  6. concentrationThe organic layer was concentrated in vacuo
  7. customThe product 20 was purified
  8. washeluting with 9:1 hexanes/EtOAc

Sources & evidence

ORD record
ord-82525f16062d4ecd8c195b9dbb5bfd4f
Source dataset
uspto-grants-2016_09
Patent number
US09434742B1

Reaction notes

Loading…