Potassium Carbonate → HCID 22017594, compound

HRID 269731Notes

Reaction equation

Cl.[CH3:2][C:3]1[O:7][C:6]([CH:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[N:5][N:4]=1.Br[C:15]1[N:20]=[CH:19][CH:18]=[CH:17][N:16]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:2][C:3]1[O:7][C:6]([CH:8]2[CH2:13][CH2:12][N:11]([C:15]3[N:20]=[CH:19][CH:18]=[CH:17][N:16]=3)[CH2:10][CH2:9]2)=[N:5][N:4]=1

Participants

Conditions

Temperature: 60 °C

Procedure

4-(5-Methyl-[1,3,4]oxadiazole-2-yl)-piperidine hydrochloride (203 mg, 1 mmol) (see reference WO 0039125, preparation 43) was added to a solution of 2-bromopyrimidine (207 mg, 1.3 mmol) and potassium carbonate (207 mg, 1.5 mmol) in N,N-dimethylformamide (0.5 mL). The solution was heated to 60° C. for 4 hours, before cooling and stirring at room temperature for 18 hours. The solvent was evaporated under reduced pressure, and the residue partitioned between water and dichloromethane. The aqueous layer was extracted with dichloromethane, and the combined organic layers were washed with brine, before being dried over magnesium sulphate and evaporated under reduced pressure. The residue was purified by chromatography on silica gel (25 g) eluting with dichloromethane and methanol (97.5:2.5) to give the title compound as a crystalline solid (75 mg).

Workup

temperaturebefore cooling
customThe solvent was evaporated under reduced pressure
customthe residue partitioned between water and dichloromethane
extractionThe aqueous layer was extracted with dichloromethane
washthe combined organic layers were washed with brine
dry with materialbefore being dried over magnesium sulphate
customevaporated under reduced pressure
customThe residue was purified by chromatography on silica gel (25 g)
washeluting with dichloromethane and methanol (97.5:2.5)

Sources & evidence

ORD record: ord-c00f90edd79d41f2ae5b36a183cdf370
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07449462B2

Reaction notes

Loading…