Tetramethyltin → 3-(1,5,7-trimethyl-2,4-dioxo-6-(3-(trifluoromethoxy)phenyl)-1H-pyrrolo[3,2-d]pyrimidin-3(2H,4H,5H)-yl)propyl acetate

HRID 60352Notes

Reaction equation

HRID 60352 reaction equation
[C:1]([O:4][CH2:5][CH2:6][CH2:7][N:8]1[C:13](=[O:14])[C:12]2[N:15]([CH3:30])[C:16]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([O:25][C:26]([F:29])([F:28])[F:27])[CH:20]=3)=[C:17](Br)[C:11]=2[N:10]([CH3:31])[C:9]1=[O:32])(=[O:3])[CH3:2].[CH3:33][Sn](C)(C)C>CN(C=O)C.CC(=O)OCC.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:1]([O:4][CH2:5][CH2:6][CH2:7][N:8]1[C:13](=[O:14])[C:12]2[N:15]([CH3:30])[C:16]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([O:25][C:26]([F:29])([F:28])[F:27])[CH:20]=3)=[C:17]([CH3:33])[C:11]=2[N:10]([CH3:31])[C:9]1=[O:32])(=[O:3])[CH3:2]

Participants

7

Reactant 2

HCID 11661TetramethyltinHCID 1188637713-(7-bromo-1,5-dimethyl-2,4-dioxo-6-(3-(trifluoromethoxy)phenyl)-1H-pyrrolo[3,2-d]pyrimidin-3(2H,4H,5H)-yl)propyl acetate

Product 1

HCID 1188637683-(1,5,7-trimethyl-2,4-dioxo-6-(3-(trifluoromethoxy)phenyl)-1H-pyrrolo[3,2-d]pyrimidin-3(2H,4H,5H)-yl)propyl acetateYield 91.8%

Reagents, catalysts & solvents 4

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-(7-bromo-1,5-dimethyl-2,4-dioxo-6-(3-(trifluoromethoxy)phenyl)-1H-pyrrolo[3,2-d]pyrimidin-3(2H,4H,5H)-yl)propyl acetate (25 mg, 0.05 mmol) in DMF (1 mL) was added tetramethylstannane (26.7 mg, 0.15 mmol) and Pd(PPh3)2Cl2 (5 mg). The reaction was heated at 120° C. (MW) for 45 min, cooled to RT then diluted with EA (5 mL) and water (5 mL). The organic layer was dried over Na2SO4 and concentrated to a residue was purified by chromatography eluted with PE/EA (5:1 to 1:1) to give 3-(1,5,7-trimethyl-2,4-dioxo-6-(3-(trifluoromethoxy)phenyl)-1H-pyrrolo[3,2-d]pyrimidin-3(2H,4H,5H)-yl)propyl acetate (20 mg, 91.8% yield) as an oil. LCMS: MH+ 454 and TR=1.625 min. Used without further purification.

Workup

  1. temperatureThe reaction was heated at 120° C. (MW) for 45 min
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated to a residue
  4. customwas purified by chromatography
  5. washeluted with PE/EA (5:1 to 1:1)

Sources & evidence

ORD record
ord-b5e56bf261424cffb185e8bef0453ff2
Source dataset
uspto-grants-2016_09
Patent number
US09440983B2

Reaction notes

Loading…