5-Methylfurfural → HCID 77105033, compound

HRID 2201171Notes

Reaction equation

HRID 2201171 reaction equation
[SH:1][CH2:2][CH2:3][N:4]1[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:11]2[C:6]([N:7]([CH3:22])[C:8](=[O:21])[N:9]([CH3:20])[C:10]2=[O:19])=[CH:5]1.[O-]S(C(F)(F)F)(=O)=O.[Bi+3].[O-]S(C(F)(F)F)(=O)=O.[O-]S(C(F)(F)F)(=O)=O.[CH3:48][C:49]1[O:53][C:52]([CH:54]=O)=[CH:51][CH:50]=1>C1(C)C=CC=CC=1>[CH3:22][N:7]1[C:6]2=[C:5]3[N:4]([C:12]([C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=4)=[C:11]2[C:10](=[O:19])[N:9]([CH3:20])[C:8]1=[O:21])[CH2:3][CH2:2][S:1][CH:54]3[C:52]1[O:53][C:49]([CH3:48])=[CH:50][CH:51]=1

Participants

5

Reactant 3

HCID 120975-MethylfurfuralHCID 9917655Bi(OTf)3HCID 86723416HCID 86723416, compound2×

Product 1

HCID 77105033HCID 77105033, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To 6-(2-mercapto-ethyl)-1,3-dimethyl-5-phenyl-1,6-dihydro-pyrrolo[3,4-d]pyrimidine-2,4-dione (Intermediate A) (207 mg, 0.656 mmol) and bismuth triflate (43.1 mg, 0.066 mmol) in toluene (5 ml) was added 5-methylfuran-2-carbaldehyde (commercial) (0.065 ml, 0.656 mmol) the mixture heated to 100° C. for 1 hour. The reaction mixture was cooled to RT and the solvent was removed under reduced pressure. The residue was partitioned between EtOAc (20 mL) and water (20 mL) and the phases separated. The aqueous phase was extracted with EtOAc (2×20 ml) the combined organic phases were dried over magnesium sulfate and the solvent removed under vacuum. Purification by chromatography on silica, eluting with 0-50% EtOAc/hexane gave the title compound.

Workup

  1. temperatureThe reaction mixture was cooled to RT
  2. customthe solvent was removed under reduced pressure
  3. customThe residue was partitioned between EtOAc (20 mL) and water (20 mL)
  4. customthe phases separated
  5. extractionThe aqueous phase was extracted with EtOAc (2×20 ml) the combined organic phases
  6. dry with materialwere dried over magnesium sulfate
  7. customthe solvent removed under vacuum
  8. customPurification by chromatography on silica
  9. washeluting with 0-50% EtOAc/hexane

Sources & evidence

ORD record
ord-4d6464c705f7477b9954b5b9a76cfedc
Source dataset
uspto-grants-2016_06
Patent number
US09359381B2

Reaction notes

Loading…