Triethylamine → 6-((R)-2-Hydroxy-1-methyl-ethyl)-1,3-dimethyl-5-phenyl-1,6-dihydro-pyrrolo[3,4-d]pyrimidine-2,4-dione

HRID 624604Notes

Reaction equation

HRID 624604 reaction equation
N[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.C(N(CC)CC)C.N[C@H](C)[CH2:32][OH:33]>CCO>[OH:33][CH2:32][C@H: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)[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 80308(R)-(-)-2-Amino-1-propanolHCID 867228796-(2-Amino-ethyl)-1,3-dimethyl-5-phenyl-1,6-dihydro-pyrrolo[3,4-d]pyrimidine-2,4-dione2×

Product 1

HCID 867229246-((R)-2-Hydroxy-1-methyl-ethyl)-1,3-dimethyl-5-phenyl-1,6-dihydro-pyrrolo[3,4-d]pyrimidine-2,4-dione

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

5-Benzoyl-6-(bromomethyl)-1,3-dimethyl-1H-pyrimidine-2,4-dione (Intermediate A step 3) (200 mg 0.59 mmol), triethylamine (82 μl, 0.59 mmol) and (R)-2-aminopropan-1-ol (45 mg, 0.59 mmol) (commercial) were combined in EtOH (2 mL). The mixture was heated at 100° C. under microwave irradiation for 1 hour. The solvent was evaporated under reduced pressure. The solid residue dissolved in DCM and water and extracted (×3). The combined organic phases were washed with water, passed through a hydrophobic frit and evaporated under reduced pressure to afford the title compound as an off-white solid.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. dissolutionThe solid residue dissolved in DCM
  3. extractionwater and extracted (×3)
  4. washThe combined organic phases were washed with water
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-e01b9c3653e4479ebf5e200fa52f331c
Source dataset
uspto-grants-2016_04
Patent number
US09303035B2

Reaction notes

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