Phosphorus oxychloride → 5-Chloro-7-(2,4-dichlorophenyl)-2-[1-(propan-2-yl)piperidin-4-yl][1,2,4]triazolo[1,5-c]pyrimidine

HRID 2088674

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[NH:14][C:13](=O)[N:12]2[N:16]=[C:17]([CH:19]3[CH2:24][CH2:23][N:22]([CH:25]([CH3:27])[CH3:26])[CH2:21][CH2:20]3)[N:18]=[C:11]2[CH:10]=1.C(=O)(O)[O-].[Na+].P(Cl)(Cl)([Cl:35])=O>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[Cl:35][C:13]1[N:12]2[N:16]=[C:17]([CH:19]3[CH2:24][CH2:23][N:22]([CH:25]([CH3:27])[CH3:26])[CH2:21][CH2:20]3)[N:18]=[C:11]2[CH:10]=[C:9]([C:3]2[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=2[Cl:1])[N:14]=1

Participants

Conditions

Temperature: 120 °C

Procedure

530 mg (1.30 mmol) of 7-(2,4-dichlorophenyl)-2-[1-(1-methylethyl)piperidin-4-yl][1,2,4]-triazolo[1,5-c]pyrimidin-5(6H)-one were initially charged in phosphorus oxychloride (16 ml), and 1.19 g (5.22 mmol) of benzyltriethylammonium chloride were added. The mixture was then stirred at 120° C. for 2.5 h. The reaction mixture was poured onto saturated aqueous sodium bicarbonate solution (150 ml), and solid sodium bicarbonate was added until a pH of 7 had been reached. The mixture was extracted with dichloromethane (3×50 ml), and the combined organic phases were washed with water (50 ml), dried over magnesium sulfate and concentrated. This gave 502 mg (89% of theory) of the product as a solid.

Workup

additionwas added until a pH of 7
extractionThe mixture was extracted with dichloromethane (3×50 ml)
washthe combined organic phases were washed with water (50 ml)
dry with materialdried over magnesium sulfate
concentrationconcentrated

Sources & evidence

ORD record: ord-5e3c396978ab475f8103556eab6cfa93
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08436003B2

Linked notes

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