Water → 6-(2-chloropyrimidin-4-yloxy)-N,2-dimethylbenzofuran-3-carboxamide

HRID 16239

Reaction equation

C(=O)([O-])[O-].[K+].[K+].[OH:7][C:8]1[CH:21]=[CH:20][C:11]2[C:12]([C:16]([NH:18][CH3:19])=[O:17])=[C:13]([CH3:15])[O:14][C:10]=2[CH:9]=1.[Cl:22][C:23]1[N:28]=[C:27](Cl)[CH:26]=[CH:25][N:24]=1.O>CN(C=O)C>[Cl:22][C:23]1[N:28]=[C:27]([O:7][C:8]2[CH:21]=[CH:20][C:11]3[C:12]([C:16]([NH:18][CH3:19])=[O:17])=[C:13]([CH3:15])[O:14][C:10]=3[CH:9]=2)[CH:26]=[CH:25][N:24]=1

Participants

Conditions

Temperature: 60 °C

Procedure

Potassium carbonate (1.5 mmol) was added to a solution of 6-hydroxy-N,2-dimethylbenzofuran-3-carboxamide (1 mmol) in 5 ml DMF. After 30 mins, 2,4-dichloropyrimidine (1 mmol) was added and the reaction mixture was stirred overnight at 60° C. Water was added. The resultant solid was filtered, washed with water, and dried to give 6-(2-chloropyrimidin-4-yloxy)-N,2-dimethylbenzofuran-3-carboxamide in a yield of 82%, as a solid, which was used in the next step without further purification.

Workup

filtrationThe resultant solid was filtered
washwashed with water
customdried

Sources & evidence

ORD record: ord-cb86a50e09fd480585599e4ca3dbb9b6
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07737157B2

Linked notes

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