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

HRID 60362Notes

Reaction equation

HRID 60362 reaction equation
[C:1]([O:4][CH2:5][CH2:6][CH2:7][N:8]1[C:13](=[O:14])[C:12]2[NH:15][C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([O:24][C:25]([F:28])([F:27])[F:26])[CH:19]=3)=[CH:17][C:11]=2[N:10]([CH3:29])[C:9]1=[O:30])(=[O:3])[CH3:2].[Br:31]Br>CC(O)=O.CC(=O)OCC.O>[C:1]([O:4][CH2:5][CH2:6][CH2:7][N:8]1[C:13](=[O:14])[C:12]2[NH:15][C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([O:24][C:25]([F:26])([F:27])[F:28])[CH:19]=3)=[C:17]([Br:31])[C:11]=2[N:10]([CH3:29])[C:9]1=[O:30])(=[O:3])[CH3:2]

Participants

6

Reactant 2

HCID 24408BromineHCID 1188637703-(1-methyl-2,4-dioxo-6-(3-(trifluoromethoxy)phenyl)-1H-pyrrolo[3,2-d]pyrimidin-3(2H,4H,5H)-yl)propyl acetate2×

Product 1

HCID 1188637793-(7-bromo-1-methyl-2,4-dioxo-6-(3-(trifluoromethoxy)phenyl)-1H-pyrrolo[3,2-d]pyrimidin-3(2H,4H,5H)-yl)propyl acetateYield 74.4%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-(1-methyl-2,4-dioxo-6-(3-(trifluoromethoxy)phenyl)-1H-pyrrolo[3,2-d]pyrimidin-3(2H,4H,5H)-yl)propyl acetate (See Intermediate 1, 170 mg, 0.40 mmol) in HOAc (3 mL) was added Br2 (76.6 mg, 0.48 mmol). The reaction was stirred at RT for 2 h then diluted with EA (10 mL) and water (5 mL). The organic layer was washed with water (3×20 mL), dried over Na2SO4 and concentrated to a residue which was purified by chromatography eluted with PE/EA (5:1) to give 3-(7-bromo-1-methyl-2,4-dioxo-6-(3-(trifluoromethoxy)phenyl)-1H-pyrrolo[3,2-d]pyrimidin-3(2H,4H,5H)-yl)propyl acetate (150 mg, 74.4% yield) as a yellow oil. LCMS: MH+ 504 and TR=1.739 min.

Workup

  1. washThe organic layer was washed with water (3×20 mL)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated to a residue which
  4. customwas purified by chromatography
  5. washeluted with PE/EA (5:1)

Sources & evidence

ORD record
ord-a103a3bbedbb4d86a0deff659dbbbf21
Source dataset
uspto-grants-2016_09
Patent number
US09440983B2

Reaction notes

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