Triethylamine → (R)-5-(3-Chlorophenyl)-6-(2,3-dihydroxypropyl)-1,3-dimethyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione

HRID 624562Notes

Reaction equation

Br[CH2:2][C:3]1[N:8]([CH3:9])[C:7](=[O:10])[N:6]([CH3:11])[C:5](=[O:12])[C:4]=1[C:13](=O)[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[CH:15]=1.[NH2:22][CH2:23][C@@H:24]([OH:27])[CH2:25][OH:26].C(N(CC)CC)C>CCO>[Cl:20][C:16]1[CH:15]=[C:14]([C:13]2[N:22]([CH2:23][C@@H:24]([OH:27])[CH2:25][OH:26])[CH:2]=[C:3]3[C:4]=2[C:5](=[O:12])[N:6]([CH3:11])[C:7](=[O:10])[N:8]3[CH3:9])[CH:19]=[CH:18][CH:17]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 6-(bromomethyl)-5-(3-chlorobenzoyl)-1,3-dimethylpyrimidine-2,4(1H,3H)-dione (2 g, 5.38 mmol), (R)-3-aminopropane-1,2-diol (0.490 g, 5.38 mmol) and triethylamine (0.750 ml, 5.38 mmol) in EtOH (17.94 ml) was heated under microwave irradiation at 100° C. for 1 hour. The mixture was evaporated under vacuum and the residue partitioned between DCM (20 mL) and 1M HCl (20 mL). The phases were separated and the organic phase was washed with water (2×20 mL). The organic phase was passed through a hydrophobic frit and evaporate under vacuum to afford the title compound.

Workup

customThe mixture was evaporated under vacuum
customthe residue partitioned between DCM (20 mL) and 1M HCl (20 mL)
customThe phases were separated
washthe organic phase was washed with water (2×20 mL)
customevaporate under vacuum

Sources & evidence

ORD record: ord-6fc374320c3840aba2337dfc60c25733
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09303035B2

Reaction notes

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