Cesium carbonate → N-{3-[6-(6-Amino-pyridin-3-yl)-2-morpholin-4-yl-pyrimidin-4-yl]pyridin-2-yl}-methanesulfonamide

HRID 1043803Notes

Reaction equation

F[C:2]1[C:7]([C:8]2[N:13]=[C:12]([N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)[N:11]=[C:10]([C:20]3[CH:21]=[CH:22][C:23]([NH2:26])=[N:24][CH:25]=3)[CH:9]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.[CH3:27][S:28]([NH2:31])(=[O:30])=[O:29].C([O-])([O-])=O.[Cs+].[Cs+]>CN1C(=O)CCC1>[NH2:26][C:23]1[N:24]=[CH:25][C:20]([C:10]2[N:11]=[C:12]([N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)[N:13]=[C:8]([C:7]3[C:2]([NH:31][S:28]([CH3:27])(=[O:30])=[O:29])=[N:3][CH:4]=[CH:5][CH:6]=3)[CH:9]=2)=[CH:21][CH:22]=1

Participants

Conditions

Temperature: 125 °C

Procedure

To a solution of 5-[6-(2-fluoro-pyridin-3-yl)-2-morpholin-4-yl-pyrimidin-4-yl]-pyridin-2-ylamine (200 mg, 0.57 mmol) and methanesulfonamide (216 mg, 2.3 mmol) in NMP (8 mL) was added Cs2CO3 (372 mg, 1.1 mmol). The solution was heated at 125° C. for 4 hours. The reaction mixture was cooled to room temperature, filtered and purified by reverse phase preparatory HPLC to give the title compound. LC/MS (m/z): 428.3 (MH+), Rt 1.80 minutes.

Workup

temperatureThe reaction mixture was cooled to room temperature
filtrationfiltered
custompurified by reverse phase preparatory HPLC

Sources & evidence

ORD record: ord-5517b8eb6d89439bb70f7cd5c659cb8e
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08563549B2

Reaction notes

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