Iodine chloride → 4-Chloro-7-cyclopentyl-5-iodo-7H-pyrrolo[2,3-d]pyrimidine

HRID 2114607Notes

Reaction equation

HRID 2114607 reaction equation
[Cl:1][C:2]1[C:3]2[CH:10]=[CH:9][N:8]([CH:11]3[CH2:15][CH2:14][CH2:13][CH2:12]3)[C:4]=2[N:5]=[CH:6][N:7]=1.[I:16]Cl>>[I:16][C:10]1[C:3]2[C:2]([Cl:1])=[N:7][CH:6]=[N:5][C:4]=2[N:8]([CH:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)[CH:9]=1

Participants

3

Reactant 2

HCID 24640Iodine chlorideHCID 5198484-Chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 195974344-Chloro-7-cyclopentyl-5-iodo-7H-pyrrolo[2,3-d]pyrimidine

Procedure

To a stirred solution of 4-Chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidine (1A, 116 g, 0.52 mole) in 1200 mL CH2CL2 was slowly added a dark brown solution of iodine monochloride (1.0 M, 785 mL) at room temperature over 30 minutes. The reaction mixture was refluxed for 22 h, cooled to room temperature and concentrated. The residue was redissolved in EtOAc, washed with saturated Na2SO3, H2O and brine. The organic layer was dried over Na2SO4 and concentrated. The residue was then recrystalized from i-PrOH to furnish 95 g white crystalline product.

Workup

  1. temperatureThe reaction mixture was refluxed for 22 h
  2. concentrationconcentrated
  3. dissolutionThe residue was redissolved in EtOAc
  4. washwashed with saturated Na2SO3, H2O and brine
  5. dry with materialThe organic layer was dried over Na2SO4
  6. concentrationconcentrated
  7. customThe residue was then recrystalized from i-PrOH

Sources & evidence

ORD record
ord-84a8e4e8c6224495ae55c16de94ee61b
Source dataset
uspto-grants-2008_10
Patent number
US07435739B2

Reaction notes

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