Potassium ethanethioate → HCID 90218191, compound

HRID 2201202Notes

Reaction equation

CS(O[CH:6]([CH2:16][N:17]1[C:25]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[C:24]2[C:19]([N:20]([CH3:35])[C:21](=[O:34])[N:22]([CH3:33])[C:23]2=[O:32])=[CH:18]1)[CH2:7][O:8][Si:9]([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10])(=O)=O.[C:36]([O-:39])(=[S:38])[CH3:37].[K+]>CN(C=O)C>[C:36](=[O:39])([S:38][CH:6]([CH2:16][N:17]1[C:25]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)=[C:24]2[C:19]([N:20]([CH3:35])[C:21](=[O:34])[N:22]([CH3:33])[C:23]2=[O:32])=[CH:18]1)[CH2:7][O:8][Si:9]([C:12]([CH3:15])([CH3:13])[CH3:14])([CH3:11])[CH3:10])[CH3:37]

Participants

Conditions

Temperature: 70 °C

Procedure

1-((tert-Butyldimethylsilyl)oxy)-3-(1,3-dimethyl-2,4-dioxo-5-phenyl-3,4-dihydro-1H-pyrrolo[3,4-d]pyrimidin-6(2H)-yl)propan-2-yl methanesulfonate (step 3)(1.3 g, 2.63 mmol) in dry DMF (20 ml) was treated with potassium thioacetate (1.5 g, 13.1 mmol). The resulting solution stirred for 7 h at 70° C. and at RT for 3 days. The mixture was heated at 70° C. overnight and after cooling to RT, the mixture was partitioned between EtOAc (100 ml) and water (150 ml). The layers were separated and the aqueous was extracted with EtOAc (×3). The organics were combined, washed with water, brine (×3), passed through a hydrophobic frit and concentrated in vacuo to yield the title compound as a brown oil;

Workup

temperatureThe mixture was heated at 70° C. overnight
temperatureafter cooling to RT
customthe mixture was partitioned between EtOAc (100 ml) and water (150 ml)
customThe layers were separated
extractionthe aqueous was extracted with EtOAc (×3)
washwashed with water, brine (×3)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-66c45e14383e40e9a9b00f7a505593b5
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09359381B2

Reaction notes

Loading…