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

HRID 1786939Notes

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 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 washed with ethanol
customdried under reduced pressure at 60° C.

Sources & evidence

ORD record: ord-f73f8bea7c904e2399764dcdefce25f6
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07507740B2

Reaction notes

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