Ethanolamine → 6-(2-Hydroxyethyl)-1,3-dimethyl-5-phenyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione

HRID 624603Notes

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(CN)[OH:24].C(Cl)Cl.O>CCO>[OH:24][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

Participants

Conditions

Temperature: 100 °C

Procedure

5-Benzoyl-6-(bromomethyl)-1,3-dimethylpyrimidine-2,4(1H,3H)-dione (Intermediate A step 3) (400 mg 1.19 mmol) in EtOH (4 mL) was treated with TEA (0.16 mL, 1.19 mmol) and ethanolamine (72.5 mg, 1.19 mmol). The mixture was heated to 100° C. for 1 h under microwave irradiation. A further portion of ethanolamine (96 μL) was added and heating continued for a further 20 min. The reaction was poured into DCM (75 mL) and water (75 mL). The layers were separated and the aqueous phase extracted with DCM (2×50 mL). The combined organic phases were washed with water (2×50 mL), then passed through a hydrophobic frit. The solvent was removed under reduced pressure affording a pale yellow solid. The solid was triturated in hot EtOH and allowed to cool. The title product was collected by reduced pressure filtration as a white powder.

Workup

temperatureheating
customThe layers were separated
extractionthe aqueous phase extracted with DCM (2×50 mL)
washThe combined organic phases were washed with water (2×50 mL)
customThe solvent was removed under reduced pressure
customaffording a pale yellow solid
customThe solid was triturated in hot EtOH
temperatureto cool
filtrationThe title product was collected by reduced pressure filtration as a white powder

Sources & evidence

ORD record: ord-f0887eb823ff4bd4a7161f54e58a2c3b
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09303035B2

Reaction notes

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