4-[({3-[2-(t-butyldimethylsilanyloxy)ethoxy]-2-fluoro-5-methoxyphenyl}-(5-oxo-1-pyrimidin-2-yl-4,5-dihydro-1H-[1,2,4]triazol-3-yl)methyl)amino]benzonitrile → 4-({[2-fluoro-3-(2-hydroxyethoxy)-5-methoxyphenyl]-(5-oxo-1-pyrimidin-2-yl-4,5-dihydro-1H-[1,2,4]triazol-3-yl)methyl}amino)benzonitrile

HRID 1161543Notes

Reaction equation

[Si]([O:8][CH2:9][CH2:10][O:11][C:12]1[C:13]([F:42])=[C:14]([CH:20]([NH:33][C:34]2[CH:41]=[CH:40][C:37]([C:38]#[N:39])=[CH:36][CH:35]=2)[C:21]2[NH:25][C:24](=[O:26])[N:23]([C:27]3[N:32]=[CH:31][CH:30]=[CH:29][N:28]=3)[N:22]=2)[CH:15]=[C:16]([O:18][CH3:19])[CH:17]=1)(C(C)(C)C)(C)C>C(O)(=O)C.O>[F:42][C:13]1[C:12]([O:11][CH2:10][CH2:9][OH:8])=[CH:17][C:16]([O:18][CH3:19])=[CH:15][C:14]=1[CH:20]([NH:33][C:34]1[CH:35]=[CH:36][C:37]([C:38]#[N:39])=[CH:40][CH:41]=1)[C:21]1[NH:25][C:24](=[O:26])[N:23]([C:27]2[N:28]=[CH:29][CH:30]=[CH:31][N:32]=2)[N:22]=1

Participants

Conditions

Temperature: 50 °C

Procedure

After dissolving 3.4 g of 4-[({3-[2-(t-butyldimethylsilanyloxy)ethoxy]-2-fluoro-5-methoxyphenyl}-(5-oxo-1-pyrimidin-2-yl-4,5-dihydro-1H-[1,2,4]triazol-3-yl)methyl)amino]benzonitrile in 100 ml of acetic acid, 5 ml of water was added and the mixture was stirred overnight at 50° C. The reaction mixture was concentrated, and the residue was purified by NAM silica gel column chromatography (methanol-ethyl acetate) to give the title compound (2.25 g) as a light yellow solid.

Workup

additionwas added
concentrationThe reaction mixture was concentrated
customthe residue was purified by NAM silica gel column chromatography (methanol-ethyl acetate)

Sources & evidence

ORD record: ord-97cb8969299944dfb1b26a25e51b787f
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07816522B2

Reaction notes

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