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Phosphorus oxychloride → ethyl 4-(4-chloro-5H-pyrrolo[3,2-d]pyrimidin-6-yl)benzoate hydrochloride

HRID 1926026
Notes
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Reaction equation

HRID 1926026 reaction equation
O=[C:2]1[NH:7][CH:6]=[N:5][C:4]2[CH:8]=[C:9]([C:11]3[CH:21]=[CH:20][C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:13][CH:12]=3)[NH:10][C:3]1=2.P(Cl)(Cl)([Cl:24])=O>O1CCOCC1>[ClH:24].[Cl:24][C:2]1[C:3]2[NH:10][C:9]([C:11]3[CH:21]=[CH:20][C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:13][CH:12]=3)=[CH:8][C:4]=2[N:5]=[CH:6][N:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 136354574ethyl 4-(4-oxo-4,5-dihydro-3H-pyrrolo[3,2-d]pyrimidin-6-yl)benzoate

Product 1

HCID 86615760ethyl 4-(4-chloro-5H-pyrrolo[3,2-d]pyrimidin-6-yl)benzoate hydrochlorideYield 94.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of ethyl 4-(4-oxo-4,5-dihydro-3H-pyrrolo[3,2-d]pyrimidin-6-yl)benzoate (2.97 g) and phosphoryl chloride (16.45 g) was stirred at 110° C. for 1 hr, dioxane (10 mL) was added and the mixture was heated under reflux for 4 hrs. After concentration under reduced pressure, ethanol (30 mL) was added to the residue and, after stirring at room temperature for 30 min, the precipitated solid was collected by filtration. The solid was washed with ethanol and dried under reduced pressure at 60° C. to give the title compound (3.34 g).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 4 hrs
  3. concentrationAfter concentration under reduced pressure, ethanol (30 mL)
  4. additionwas added to the residue
  5. stirringafter stirring at room temperature for 30 min
  6. filtrationthe precipitated solid was collected by filtration
  7. washThe solid was washed with ethanol
  8. customdried under reduced pressure at 60° C.

Sources & evidence

ORD record
ord-136430b7db384fbebe21332770bc0957
Source dataset
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08178543B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes