Sodium hydride → 1-(3-Methyl-4-(3-(2-(methylamino)pyrimidin-4-yl)pyridin-2-yloxy)phenyl)imidazolidin-2-one
Reaction equation
[H-].[Na+].Cl[CH2:4][CH2:5][NH:6][C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]2[C:22]([C:23]3[CH:28]=[CH:27][N:26]=[C:25]([NH:29][CH3:30])[N:24]=3)=[CH:21][CH:20]=[CH:19][N:18]=2)=[C:12]([CH3:31])[CH:11]=1)=[O:8]>C1COCC1>[CH3:31][C:12]1[CH:11]=[C:10]([N:9]2[CH2:4][CH2:5][NH:6][C:7]2=[O:8])[CH:15]=[CH:14][C:13]=1[O:16][C:17]1[C:22]([C:23]2[CH:28]=[CH:27][N:26]=[C:25]([NH:29][CH3:30])[N:24]=2)=[CH:21][CH:20]=[CH:19][N:18]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a slurry of NaH (60% in mineral oil, 0.109 g, 2.73 mmol) in THF (13 mL) in a sealable tube under nitrogen was added 1-(2-chloroethyl)-3-(3-methyl-4-(3-(2-(methylamino)pyrimidin-4-yl)pyridin-2-yloxy)phenyl)urea (0.537 g, 1.30 mmol) in portions. The reaction was sealed and heated to 80 deg. C. for 3 h. The reaction was cooled to ambient temperature and was concentrated under a stream of nitrogen. The resulting solid was suspended in 50 mL water, acidified to pH 1 with 6 N HCl, and filtered. The solid was rinsed with water, diethyl ether, and dried in vacuo to give 1-(3-methyl-4-(3-(2-(methylamino)pyrimidin-4-yl)pyridin-2-yloxy)phenyl)imidazolidin-2-one as a tan solid. MS m/z=377 [M+1]+. Calc'd for C20H20N6O2: 376.16.
Workup
- customThe reaction was sealed
- temperatureheated to 80 deg. C
- concentrationwas concentrated under a stream of nitrogen
- filtrationfiltered
- washThe solid was rinsed with water, diethyl ether
- customdried in vacuo
Sources & evidence
- ORD record
- ord-53adea37319742c78c85474b3b8fcdbd
- Source dataset
- uspto-grants-2011_02
- Patent number
- US07880000B2
Reaction notes
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