Sodium Dithionite → 3-(6-(3-chlorophenyl)-1-methyl-2,4-dioxo-1H-pyrrolo[3,2-d]pyrimidin-3(2H,4H,5H)-yl)propylacetate

HRID 60347Notes

Reaction equation

HRID 60347 reaction equation
[C:1]([O:4][CH2:5][CH2:6][CH2:7][N:8]1[C:13](=[O:14])[C:12]([N+:15]([O-])=O)=[C:11](/[CH:18]=[CH:19]/[C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[CH:21]=2)[N:10]([CH3:27])[C:9]1=[O:28])(=[O:3])[CH3:2].[O-]S(S([O-])=O)=O.[Na+].[Na+]>C(O)=O.CC(=O)OCC.O>[Cl:26][C:22]1[CH:21]=[C:20]([C:19]2[NH:15][C:12]3[C:13](=[O:14])[N:8]([CH2:7][CH2:6][CH2:5][O:4][C:1](=[O:3])[CH3:2])[C:9](=[O:28])[N:10]([CH3:27])[C:11]=3[CH:18]=2)[CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 2

HCID 24489Sodium DithioniteHCID 118863769(E)-3-(4-(3-chlorostyryl)-3-methyl-5-nitro-2,6-dioxo-2,3-dihydropyrimidin-1(6H)-yl)propyl acetate

Product 1

HCID 1188637723-(6-(3-chlorophenyl)-1-methyl-2,4-dioxo-1H-pyrrolo[3,2-d]pyrimidin-3(2H,4H,5H)-yl)propylacetateYield 93%

Reagents, catalysts & solvents 3

HCID 284Formic AcidSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of (E)-3-(4-(3-chlorostyryl)-3-methyl-5-nitro-2,6-dioxo-2,3-dihydropyrimidin-1(6H)-yl)propyl acetate (70 mg, 0.172 mmol) in HCOOH (3 mL) was added Na2S2O4 (180.0 mg, 1.032 mmol). The reaction was heated at 110° C. for 5 h, cooled to RT then diluted with EA (20 mL) and water (20 mL). The organic layer was dried over Na2SO4 and concentrated to give 3-(6-(3-chlorophenyl)-1-methyl-2,4-dioxo-1H-pyrrolo[3,2-d]pyrimidin-3(2H,4H,5H)-yl)propylacetate (60 mg, 93.0% yield) as an oil. LCMS: MH+ 375 and TR=1.467 min. Used without further purification.

Workup

  1. temperaturecooled to RT
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-7545372e2b114f2584be303b46a5358b
Source dataset
uspto-grants-2016_09
Patent number
US09440983B2

Reaction notes

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