N-Iodosuccinimide → HCID 66791227, compound

HRID 1678237Notes

Reaction equation

HRID 1678237 reaction equation
[I:1]N1C(=O)CCC1=O.[CH3:9][N:10]([CH3:22])[CH:11]=[N:12][C:13]1[N:14]=[CH:15][C:16]2[NH:21][CH:20]=[CH:19][C:17]=2[N:18]=1>CN(C=O)C>[I:1][C:19]1[C:17]2[N:18]=[C:13]([N:12]=[CH:11][N:10]([CH3:22])[CH3:9])[N:14]=[CH:15][C:16]=2[NH:21][CH:20]=1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 66790910HCID 66790910, compound

Product 1

HCID 66791227HCID 66791227, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-Iodosuccinimide (3.2 g, 14.2 mmol) was added portionwise to an ice-cold stirred suspension of N,N-dimethyl-N′-(5H-pyrrolo[3,2-d]pyrimidin-2-yl)-formamidine (Journal of Medicinal Chemistry, 2003, 46(14), 3060-3071, 2.68 g, 14.2 mmol) in DMF (50 mL). After stirring at ambient temperature overnight, the reaction was concentrated, dissolved in DCM (40 mL) and the product was precipitated using EtOAc (250 mL). After filtration, the pale yellow powder was collected, washed with EtOAc (2×20 mL) and dried under a vacuum overnight to afford N′-(7-iodo-5H-pyrrolo[3,2-d]pyrimidin-2-yl)-N,N-dimethyl-formamidine (3.8 g, 85%) as a yellow powder; 1H NMR (DMSO-d6, 400 MHz) δ 12.38 (s, 1H), 8.74 (s, 1H), 8.04 (s, 1 H), 7.93 (s, 1H), 3.29 (s, 3H), 3.19 (s, 3H); ESI−MS [M+H]+=316.1.

Workup

  1. stirringAfter stirring at ambient temperature overnight
  2. concentrationthe reaction was concentrated
  3. dissolutiondissolved in DCM (40 mL)
  4. customthe product was precipitated
  5. filtrationAfter filtration
  6. customthe pale yellow powder was collected
  7. washwashed with EtOAc (2×20 mL)
  8. customdried under a vacuum overnight

Sources & evidence

ORD record
ord-f143ef9312744fdebe86c17b077ceeb3
Source dataset
uspto-grants-2011_08
Patent number
US08008481B2

Reaction notes

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