Cesium carbonate → 4-(2-(6-Chloropyridin-3-yloxy)pyridin-3-yl)-2-(methylthio)pyrimidine

HRID 252653

Reaction equation

C(=O)([O-])[O-].[Cs+].[Cs+].[Cl:7][C:8]1[N:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1.Cl[C:16]1[C:21]([C:22]2[CH:27]=[CH:26][N:25]=[C:24]([S:28][CH3:29])[N:23]=2)=[CH:20][CH:19]=[CH:18][N:17]=1>O>[Cl:7][C:8]1[N:13]=[CH:12][C:11]([O:14][C:16]2[C:21]([C:22]3[CH:27]=[CH:26][N:25]=[C:24]([S:28][CH3:29])[N:23]=3)=[CH:20][CH:19]=[CH:18][N:17]=2)=[CH:10][CH:9]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of cesium carbonate (5.03 g, 15.4 mmol), 6-chloropyridin-3-ol (1.00 g, 7.72 mmol), and 4-(2-chloropyridin-3-yl)-2-(methylthio)pyrimidine (1.83 g, 7.72 mmol) was sealed and heated to 120° C. overnight. The reaction was cooled slightly and poured slowly into a rapidly stirring solution of 250 mL water. A tan precipitate resulted which was collected by filtration through a 0.45 micron filter. The solid was washed 3× with water, then dried in vacuo overnight to give 4-(2-(6-chloropyridin-3-yloxy)pyridin-3-yl)-2-(methylthio)pyrimidine as a tan solid. MS m/z=331 [M+H]+. Calc'd for C15H11ClN4OS: 330.8.

Workup

customwas sealed
temperatureThe reaction was cooled slightly
customA tan precipitate resulted which
filtrationwas collected by filtration through a 0.45 micron
filtrationfilter
washThe solid was washed 3× with water
customdried in vacuo overnight

Sources & evidence

ORD record: ord-830c76f3007946d69e4f99dbc37d1451
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07868177B2

Linked notes

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