(E)-3-{4-[5-(2-fluoro-phenoxy)-oxazolo[5,4-d]pyrimidin-2-yl]-phenyl}-acrylic acid tert-butyl ester → (E)-3-{4-[5-(2-Fluoro-phenoxy)-oxazolo[5,4-d]pyrimidin-2-yl]-phenyl}-acrylic acid

HRID 81387Notes

Reaction equation

HRID 81387 reaction equation
C([O:5][C:6](=[O:32])/[CH:7]=[CH:8]/[C:9]1[CH:14]=[CH:13][C:12]([C:15]2[O:16][C:17]3[N:18]=[C:19]([O:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=4[F:31])[N:20]=[CH:21][C:22]=3[N:23]=2)=[CH:11][CH:10]=1)(C)(C)C>ClCCl.FC(F)(F)C(O)=O>[F:31][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=1[O:24][C:19]1[N:20]=[CH:21][C:22]2[N:23]=[C:15]([C:12]3[CH:11]=[CH:10][C:9](/[CH:8]=[CH:7]/[C:6]([OH:32])=[O:5])=[CH:14][CH:13]=3)[O:16][C:17]=2[N:18]=1

Participants

4

Reactant 1

HCID 86679071(E)-3-{4-[5-(2-fluoro-phenoxy)-oxazolo[5,4-d]pyrimidin-2-yl]-phenyl}-acrylic acid tert-butyl ester

Product 1

HCID 53312044(E)-3-{4-[5-(2-Fluoro-phenoxy)-oxazolo[5,4-d]pyrimidin-2-yl]-phenyl}-acrylic acidYield 122%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 145 mg of (E)-3-{4-[5-(2-fluoro-phenoxy)-oxazolo[5,4-d]pyrimidin-2-yl]-phenyl}-acrylic acid tert-butyl ester in 2 ml of dichloromethane and 1 ml of trifluoroacetic acid was stirred at room temperature for 1.5 h. Then the mixture was concentrated in vacuo and freeze-dried. 154 mg of the title compound were obtained. LC/MS (method LC1): Rt=1.25 min; m/z=378.08 [M+H]+

Workup

  1. concentrationThen the mixture was concentrated in vacuo
  2. customfreeze-dried

Sources & evidence

ORD record
ord-e513617e83ae46519bf1a622365650a3
Source dataset
uspto-grants-2014_09
Patent number
US08846692B2

Reaction notes

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