Water → 5-Bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine

HRID 2039735Notes

Reaction equation

HRID 2039735 reaction equation
[Cl:1][C:2]1[C:3]2[CH:10]=[CH:9][NH:8][C:4]=2[N:5]=[CH:6][N:7]=1.C1C(=O)N([Br:18])C(=O)C1.O>C(Cl)Cl>[Br:18][C:10]1[C:3]2[C:2]([Cl:1])=[N:7][CH:6]=[N:5][C:4]=2[NH:8][CH:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 53566827H-Pyrrolo(2,3-d)pyrimidine, 4-chloro-

Product 1

HCID 53807105-Bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (5.91 g, 38 mmol) in DCM (250 mL) was added NBS (7.93 g, 44 mmol). The suspension was stirred at room temperature for 3 hours. Water (200 mL) was added to the reaction mixture. The mixture was sonicated for 5 min. The solid was collected by filtration and washed with water, then taken into 100 mL of MeOH. The suspension was sonicated for 3 min. The solid was collected by filtration as the desired product (6.47 g, 72%). LCMS[M+1]: 232.

Workup

  1. customThe mixture was sonicated for 5 min
  2. filtrationThe solid was collected by filtration
  3. washwashed with water
  4. customThe suspension was sonicated for 3 min
  5. filtrationThe solid was collected by filtration as the desired product (6.47 g, 72%)

Sources & evidence

ORD record
ord-f63218e6ae6a427faa5c4dfce70b68cb
Source dataset
uspto-grants-2013_11
Patent number
US08580803B2

Reaction notes

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