Chlorosuccinimide → 2,5-Dichloro-7-cyclopentyl-6-methyl-7H-pyrrolo[2,3-d]pyrimidine

HRID 2189310Notes

Reaction equation

HRID 2189310 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[CH:10]=[C:9]([CH3:11])[N:8]([CH:12]3[CH2:16][CH2:15][CH2:14][CH2:13]3)[C:6]=2[N:7]=1.[Cl:17]N1C(=O)CCC1=O>ClCCl>[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[C:10]([Cl:17])=[C:9]([CH3:11])[N:8]([CH:12]3[CH2:13][CH2:14][CH2:15][CH2:16]3)[C:6]=2[N:7]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 848197792-Chloro-7-cyclopentyl-6-methyl-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 866373452,5-Dichloro-7-cyclopentyl-6-methyl-7H-pyrrolo[2,3-d]pyrimidineYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-Chloro-7-cyclopentyl-6-methyl-7H-pyrrolo[2,3-d]pyrimidine (164 mg, 0.70 mmol) in dichloromethane (3 mL) is added N-chlorosuccinimide (0.4M in DCM, 1.1 eq) over 1 h. The reaction mixture is allowed to stir for 3 days at room temperature. The reaction mixture is diluted with dichloromethane and washed with saturated aqueous sodium bicarbonate followed by brine. The organic phase is concentrated and the crude product is purified by normal phase chromatography (SiO2, EtOAc/heptane) to obtain 2,5-Dichloro-7-cyclopentyl-6-methyl-7H-pyrrolo[2,3-d]pyrimidine (158 mg, 84%).

Workup

  1. washwashed with saturated aqueous sodium bicarbonate
  2. concentrationThe organic phase is concentrated
  3. customthe crude product is purified by normal phase chromatography (SiO2, EtOAc/heptane)

Sources & evidence

ORD record
ord-8a966c48362a4e7f89924edad6e06479
Source dataset
uspto-grants-2012_12
Patent number
US08324225B2

Reaction notes

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