5-Methylfurfural → 1,3-Dimethyl-10-(5-methylfuran-2-yl)-5-phenyl-7,8,9,10-tetrahydropyrazino[1',2':1,2]pyrrolo[3,4-d]pyrimidine-2,4(1H,3H)-dione

HRID 624555Notes

Reaction equation

HRID 624555 reaction equation
[NH2:1][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.[CH3:23][C:24]1[O:28][C:27]([CH:29]=O)=[CH:26][CH:25]=1>CCO>[CH3:22][N:7]1[C:6]2=[C:5]3[CH:29]([C:27]4[O:28][C:24]([CH3:23])=[CH:25][CH:26]=4)[NH:1][CH2:2][CH2:3][N:4]3[C:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[C:11]2[C:10](=[O:19])[N:9]([CH3:20])[C:8]1=[O:21]

Participants

4

Reactant 2

HCID 120975-Methylfurfural2×HCID 867228796-(2-Amino-ethyl)-1,3-dimethyl-5-phenyl-1,6-dihydro-pyrrolo[3,4-d]pyrimidine-2,4-dione2×

Product 1

HCID 762851491,3-Dimethyl-10-(5-methylfuran-2-yl)-5-phenyl-7,8,9,10-tetrahydropyrazino[1',2':1,2]pyrrolo[3,4-d]pyrimidine-2,4(1H,3H)-dione

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

6-(2-Amino-ethyl)-1,3-dimethyl-5-phenyl-1,6-dihydro-pyrrolo[3,4-d]pyrimidine-2,4-dione (Intermediate A) (519 mg, 1.740 mmol) in EtOH (3 mL) was treated with 5-methylfuran-2-carbaldehyde (commercial) (0.173 mL, 1.740 mmol) and heated at 100° C. for 30 min using microwave irradiation. A further portion of 5-methylfuran-2-carbaldehyde (0.173 mL, 1.740 mmol) was added and heating continued at 100° C. for 10 min. The solvent was removed under reduced pressure and purification by chromatography on silica eluting with 40-80% EtOAc in iso-hexanes afforded the title compound as a yellow solid.

Workup

  1. custommicrowave irradiation
  2. temperatureheating
  3. customThe solvent was removed under reduced pressure and purification by chromatography on silica eluting with 40-80% EtOAc in iso-hexanes

Sources & evidence

ORD record
ord-d1688877e7204abcb7beec5a6baa0c8e
Source dataset
uspto-grants-2016_04
Patent number
US09303035B2

Reaction notes

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