Benzoyl Peroxide → ethyl 3-(5-(bromomethyl)-1-methyl-2,4-dioxo-6-(3-(trifluoromethoxy)phenyl)-1,2-dihydrothieno[2,3-d]pyrimidin-3(4H)-yl)propanoate

HRID 63917Notes

Reaction equation

HRID 63917 reaction equation
[CH3:1][N:2]1[C:7]2[S:8][C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([O:18][C:19]([F:22])([F:21])[F:20])[CH:13]=3)=[C:10]([CH3:11])[C:6]=2[C:5](=[O:23])[N:4]([CH2:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])[C:3]1=[O:31].C1C(=O)N([Br:39])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl.C(Cl)Cl>[Br:39][CH2:11][C:10]1[C:6]2[C:5](=[O:23])[N:4]([CH2:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])[C:3](=[O:31])[N:2]([CH3:1])[C:7]=2[S:8][C:9]=1[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][C:19]([F:20])([F:21])[F:22])[CH:13]=1

Participants

6

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 118863112ethyl 3-(1,5-dimethyl-2,4-dioxo-6-(3-(trifluoromethoxy)phenyl)-1,2-dihydrothieno[2,3-d]pyrimidin-3 (4H)-yl)propanoate

Product 1

HCID 118863113ethyl 3-(5-(bromomethyl)-1-methyl-2,4-dioxo-6-(3-(trifluoromethoxy)phenyl)-1,2-dihydrothieno[2,3-d]pyrimidin-3(4H)-yl)propanoateYield 85.7%

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl 3-(1,5-dimethyl-2,4-dioxo-6-(3-(trifluoromethoxy)phenyl)-1,2-dihydrothieno[2,3-d]pyrimidin-3(4H)-yl)propanoate (120 mg, 0.22 mmol) in CCl4 (3 mL) was added NBS (39 mg, 0.22 mmol) followed by benzoyl peroxide (5 mg). The reaction was heated at reflux for 4 h, cooled to RT and diluted with DCM (10 mL). The mixture was washed with aq. NaHCO3 (10 mL), and brine (10 mL). The organic layer was dried over Na2SO4 and concentrated to give ethyl 3-(5-(bromomethyl)-1-methyl-2,4-dioxo-6-(3-(trifluoromethoxy)phenyl)-1,2-dihydrothieno[2,3-d]pyrimidin-3(4H)-yl)propanoate (100 mg, 85.7% yield) as an oil. LCMS: MH+ 535 and TR=2.087 min. Used without further purification.

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 4 h
  3. washThe mixture was washed with aq. NaHCO3 (10 mL), and brine (10 mL)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-20e7510941f14934acfdf1c05423ae62
Source dataset
uspto-grants-2016_09
Patent number
US09447114B2

Reaction notes

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