Bromine → 7-Bromo-4-chloro-2,6-dimethyl-5H-pyrrolo[3,2-d]pyrimidine

HRID 2208121Notes

Reaction equation

HRID 2208121 reaction equation
[Cl:1][C:2]1[C:3]2[NH:11][C:10]([CH3:12])=[CH:9][C:4]=2[N:5]=[C:6]([CH3:8])[N:7]=1.[Br:13]Br>ClCCl>[Br:13][C:9]1[C:4]2[N:5]=[C:6]([CH3:8])[N:7]=[C:2]([Cl:1])[C:3]=2[NH:11][C:10]=1[CH3:12]

Participants

4

Reactant 2

HCID 24408BromineHCID 185110614-chloro-2,6-dimethyl-5H-pyrrolo[3,2-d]pyrimidine

Product 1

HCID 866666377-Bromo-4-chloro-2,6-dimethyl-5H-pyrrolo[3,2-d]pyrimidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
10 °C

Procedure

4-Chloro-2,6-dimethyl-5H-pyrrolo[3,2-d]pyrimidine from example A7 (10.90 g; 60.00 mmol) is dissolved in dichloromethane (120 mL). The stirred mixture is cooled to 10° C. Br2 (3.08 mL; 60.00 mmol) dissolved in dichloromethane (20 mL) is added dropwise within 25 minutes. The resulting precipitate is collected by suction filtration, suspended in Na2SO3 (5% solution) (100 mL) and is stirred for 30 minutes at ambient temperature. After filtratrion the product is dissolved in acetonitrile (1000 mL), refluxed for one hour and filtered while still hot. The solvent is removed under reduced pressure until the product starts to precipitate. Precipitation of the product is completed by addition of cyclohexane and cooling to 0° C. for several hours. The solid is collected by suction filtration, washed with cyclohexane and dried in vacuum at 50° C. over night to yield the title compound as a white solid.

Workup

  1. additionis added dropwise within 25 minutes
  2. filtrationThe resulting precipitate is collected by suction filtration
  3. dissolutionis dissolved in acetonitrile (1000 mL)
  4. temperaturerefluxed for one hour
  5. filtrationfiltered while still hot
  6. customThe solvent is removed under reduced pressure until the product
  7. customto precipitate
  8. customPrecipitation of the product
  9. additionis completed by addition of cyclohexane
  10. temperaturecooling to 0° C. for several hours
  11. filtrationThe solid is collected by suction filtration
  12. washwashed with cyclohexane
  13. customdried in vacuum at 50° C. over night

Sources & evidence

ORD record
ord-f0de2a2be8dd4b1690734f206b911e03
Source dataset
uspto-grants-2016_06
Patent number
US09376442B2

Reaction notes

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