Phosphorus oxychloride → HCID 67177108, compound

HRID 1027480Notes

Reaction equation

P(Cl)(Cl)(Cl)(Cl)Cl.Cl.[Cl:8][C:9]1[CH:33]=[CH:32][C:12]([CH2:13][C:14]2[N:19]=[C:18]([OH:20])[C:17]([NH:21][C:22](=O)[C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[CH:24]=3)=[C:16]([OH:31])[N:15]=2)=[CH:11][CH:10]=1.P(Cl)(Cl)(Cl)=O>C(Cl)(Cl)Cl>[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:13][C:14]2[NH:19][C:18](=[O:20])[C:17]3[N:21]=[C:22]([C:23]4[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[CH:24]=4)[O:31][C:16]=3[N:15]=2)=[CH:32][CH:33]=1

Participants

Conditions

Temperature: 60 °C

Procedure

7.4 g of phosphorus pentachloride were added at 60° C. to a suspension of 8.9 g of N-[2-(4-chloro-benzyl)-4,6-dihydroxy-pyrimidin-5-yl]-3-fluoro-benzamide hydrochloride in 100 ml of dry chloroform. After heating at 60° C. for several hours, 5.5 g of phosphorus oxychloride were added and the reaction mixture was stirred at 75° C. for 20 h. After cooling to room temperature, the precipitate was filtered off and purified by silica gel chromatography (gradient from ethyl acetate to dichloromethane to dichloromethane/methanol 3:1). The product fractions were evaporated and the residue washed with chloroform and water and dried in an infrared dryer until constant weight to give 0.47 g of the title compound.

Workup

temperatureAfter cooling to room temperature
filtrationthe precipitate was filtered off
custompurified by silica gel chromatography (gradient from ethyl acetate to dichloromethane to dichloromethane/methanol 3:1)
customThe product fractions were evaporated
washthe residue washed with chloroform and water
customdried in an infrared dryer until constant weight

Sources & evidence

ORD record: ord-5d79beb5c93a448994d716112923e0cc
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08735387B2

Reaction notes

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