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

HRID 1926026Notes

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

Participants

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

temperaturethe mixture was heated
temperatureunder reflux for 4 hrs
concentrationAfter concentration under reduced pressure, ethanol (30 mL)
additionwas added to the residue
stirringafter stirring at room temperature for 30 min
filtrationthe precipitated solid was collected by filtration
washThe solid was washed with ethanol
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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