Phosphorus oxychloride → Ethyl 4-chloro-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylate

HRID 600463Notes

Reaction equation

HRID 600463 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:10]2[N:11]=[CH:12][N:13]=[C:14](O)[C:9]=2[NH:8][CH:7]=1)=[O:5])[CH3:2].O=P(Cl)(Cl)[Cl:18]>CCOCC>[CH2:1]([O:3][C:4]([C:6]1[C:10]2[N:11]=[CH:12][N:13]=[C:14]([Cl:18])[C:9]=2[NH:8][CH:7]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178469880HCID 178469880, compound

Product 1

HCID 52987614Ethyl 4-chloro-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylateYield 83.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
105 °C

Procedure

4,6-Diazaindole 4 (2.74 g, 13.2 mmol) was slurried in POCl3 (37 mL, 400 mmol) and heated at 105° C. for 3.5 h. The reaction mixture was cooled, diluted with Et2O (150 mL) and the resulting precipitate was collected by filtration, rinsed with EtOAc and Et2O and dried under vacuum to yield 7-chloro-4,6-diazaindole 5 (2.48 g, 11.0 mmol, 83%) as a yellow powder which was used without further purification.

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationthe resulting precipitate was collected by filtration
  3. washrinsed with EtOAc and Et2O
  4. customdried under vacuum

Sources & evidence

ORD record
ord-545997e8ed514a9aa7a354ff36f76649
Source dataset
uspto-grants-2011_03
Patent number
US07902204B2

Reaction notes

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