Potassium Carbonate → 7-bromo-4-chloro-5H-pyrrolo[3,2-d]pyrimidine

HRID 244453Notes

Reaction equation

HRID 244453 reaction equation
[Br:1][C:2]1[C:6]2[N:7]=[CH:8][NH:9][C:10](=O)[C:5]=2[NH:4][CH:3]=1.O=P(Cl)(Cl)[Cl:14].C(=O)([O-])[O-].[K+].[K+]>>[Br:1][C:2]1[C:6]2[N:7]=[CH:8][N:9]=[C:10]([Cl:14])[C:5]=2[NH:4][CH:3]=1

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 24813Phosphorus oxychlorideHCID 1357437117-Bromo-1,5-dihydro-4H-pyrrolo[3,2-D]pyrimidin-4-one

Product 1

HCID 529876607-bromo-4-chloro-5H-pyrrolo[3,2-d]pyrimidineYield 93%

Conditions

Temperature
115 °C

Procedure

A mixture of 7-bromo-3,5-dihydropyrrolo[3,2-d]pyrimidin-4-one (100 mg, 0.5 mmol) and 6 mL of POCl3 under argon was warmed at 115° C. After 3 hours, the mixture was cooled to room temperature and poured over 300 mL of ice, stirred, made basic with potassium carbonate and extracted with EtOAc. The combined organic layers were dried, filtered, and concentrated in vacuo to provide 101 mg (93%) of the desired 7-bromo-4-chloro-5H-pyrrolo[3,2-d]pyrimidine as beige solid which was used without further purification.

Workup

  1. temperaturethe mixture was cooled to room temperature
  2. extractionextracted with EtOAc
  3. customThe combined organic layers were dried
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8a64ffe74c1346c2aed45070dc8214a3
Source dataset
uspto-grants-2014_02
Patent number
US08658637B2

Reaction notes

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