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

HRID 63912Notes

Reaction equation

HRID 63912 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:25][C:11]3[N:12]([CH3:24])[C:13](=[O:23])[N:14]([CH2:17][CH2:18][C:19]([O:21][CH3:22])=[O:20])[C:15](=[O:16])[C:10]=3[C:9]=2[CH3:26])=[CH:4][CH:3]=1.C1C(=O)N([Br:34])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl.C(Cl)Cl>[Br:34][CH2:26][C:9]1[C:10]2[C:15](=[O:16])[N:14]([CH2:17][CH2:18][C:19]([O:21][CH3:22])=[O:20])[C:13](=[O:23])[N:12]([CH3:24])[C:11]=2[S:25][C:8]=1[C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1

Participants

6

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 118863098methyl 3-(6-(4-chlorophenyl)-1,5-dimethyl-2,4-dioxo-1,2-dihydrothieno[2,3-d]pyrimidin-3(4H)-yl)propanoate

Product 1

HCID 118863122methyl 3-(5-(bromomethyl)-6-(4-chlorophenyl)-1-methyl-2,4-dioxo-1,2-dihydrothieno[2,3-d]pyrimidin-3(4H)-yl)propanoateYield 100%

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 3-(6-(4-chlorophenyl)-1,5-dimethyl-2,4-dioxo-1,2-dihydrothieno[2,3-d]pyrimidin-3(4H)-yl)propanoate (25 mg, 0.0636 mmol) in CCl4 (1 mL) was added NBS (11.3 mg, 0.0636 mmol) followed by benzoyl peroxide (2 mg). The reaction was heated at reflux for 4 h, cooled to RT then diluted with DCM (10 mL). The mixture was washed with aq. NaHCO3 (5 mL) and brine (10 mL). The organic layer was dried over Na2SO4 and concentrated to give methyl 3-(5-(bromomethyl)-6-(4-chlorophenyl)-1-methyl-2,4-dioxo-1,2-dihydrothieno[2,3-d]pyrimidin-3(4H)-yl)propanoate (30 mg, 100% yield). LCMS: MH+ 473 and TR=1.907 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 (5 mL) and brine (10 mL)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e4b9f326d97b47ffa3d6585541acd0d5
Source dataset
uspto-grants-2016_09
Patent number
US09447114B2

Reaction notes

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