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

HRID 916772Notes

Reaction equation

HRID 916772 reaction equation
Cl[C:2]1[C:3]2[C:10]([I:11])=[CH:9][N:8]([CH:12]3[CH2:16][CH2:15][CH2:14][CH2:13]3)[C:4]=2[N:5]=[CH:6][N:7]=1.[OH-].[NH3:18]>O1CCOCC1>[CH:12]1([N:8]2[C:4]3[N:5]=[CH:6][N:7]=[C:2]([NH2:18])[C:3]=3[C:10]([I:11])=[CH:9]2)[CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 195974344-Chloro-7-cyclopentyl-5-iodo-7H-pyrrolo[2,3-d]pyrimidineHCID 21862953Ammonia hydroxide

Product 1

HCID 672195247-cyclopentyl-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-4-amineYield 92%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a pressure tube with dioxane (5 mL) was added 4-Chloro-7-cyclopentyl-5-iodo-7H-pyrrolo[2,3-d]pyrimidine, then ammonia hydroxide (5 mL). The pressure tube was sealed and heated at 120 C overnight. All solvents were removed via reduced pressure, and the residue were purified through flash column (methylene chloride/methanol:97/3). The product was obtained as a white solid (300 mg, 92%). MS: 329.1 (MH+); HPLC Rf: 5.018 min.; HPLC

Workup

  1. customThe pressure tube was sealed
  2. temperatureheated at 120 C overnight
  3. customAll solvents were removed via reduced pressure
  4. customthe residue were purified through flash column (methylene chloride/methanol:97/3)

Sources & evidence

ORD record
ord-c2d7eca70d6d49598af31418a38e0d9e
Source dataset
uspto-grants-2007_09
Patent number
US07271262B2

Reaction notes

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