6-((2-((4-(difluoromethoxy)phenyl)amino)pyrimidin-5-yl)methoxy)-3-(hydroxymethyl)benzo[d]oxazol-2(3H)-one → 6-((2-((4-(difluoromethoxy)phenyl)amino)pyrimidin-5-yl)methoxy)benzo[d]oxazol-2(3H)-one

HRID 77460Notes

Reaction equation

HRID 77460 reaction equation
[F:1][CH:2]([F:31])[O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]2[N:16]=[CH:15][C:14]([CH2:17][O:18][C:19]3[CH:30]=[CH:29][C:22]4[N:23](CO)[C:24](=[O:26])[O:25][C:21]=4[CH:20]=3)=[CH:13][N:12]=2)=[CH:6][CH:5]=1>CO.O>[F:31][CH:2]([F:1])[O:3][C:4]1[CH:5]=[CH:6][C:7]([NH:10][C:11]2[N:16]=[CH:15][C:14]([CH2:17][O:18][C:19]3[CH:30]=[CH:29][C:22]4[NH:23][C:24](=[O:26])[O:25][C:21]=4[CH:20]=3)=[CH:13][N:12]=2)=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 866797486-((2-((4-(difluoromethoxy)phenyl)amino)pyrimidin-5-yl)methoxy)-3-(hydroxymethyl)benzo[d]oxazol-2(3H)-one

Product 1

HCID 866797476-((2-((4-(difluoromethoxy)phenyl)amino)pyrimidin-5-yl)methoxy)benzo[d]oxazol-2(3H)-oneYield 87%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

6-((2-((4-(difluoromethoxy)phenyl)amino)pyrimidin-5-yl)methoxy)-3-(hydroxymethyl)benzo[d]oxazol-2(3H)-one (0.011 g, 0.026 mmol) was dissolved in a mixture of methanol (2 mL) and water (2 mL). The reaction mixture was sonicated for 15 min. Solvent was concentrated and the residue was lyophilized to give 6-((2-((4-(difluoromethoxy)phenyl)amino)pyrimidin-5-yl)methoxy)benzo[d]oxazol-2(3H)-one as a white solid (0.009 g, 87% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 4.99 (s, 2H) 6.82 (dd, J=8.53, 2.26 Hz, 1H) 6.94-7.32 (m, 5H) 7.79 (s, 2H) 8.59 (br. s., 2H) 9.84 (s, 1H) 11.42-11.50 (m, 1H). LCMS: R.T.=0.84 min; [M+H]+=401.0.

Workup

  1. customThe reaction mixture was sonicated for 15 min
  2. concentrationSolvent was concentrated

Sources & evidence

ORD record
ord-670e0db841da4854ad1aebe41095a5a3
Source dataset
uspto-grants-2014_09
Patent number
US08841301B2

Reaction notes

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