Cesium carbonate → HCID 59395867, compound

HRID 1097646

Reaction equation

[Cl:1][C:2]1[N:10]([CH2:11][CH:12]=[CH2:13])[C:9]2[C:8](=[O:14])[NH:7][C:6](=[O:15])[N:5]([CH2:16][CH2:17][CH2:18][C:19]([F:22])([F:21])[F:20])[C:4]=2[N:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:30][CH2:31][CH2:32][OH:33]>CN(C=O)C>[Cl:1][C:2]1[N:10]([CH2:11][CH:12]=[CH2:13])[C:9]2[C:8](=[O:14])[N:7]([CH2:30][CH2:31][CH2:32][OH:33])[C:6](=[O:15])[N:5]([CH2:16][CH2:17][CH2:18][C:19]([F:22])([F:20])[F:21])[C:4]=2[N:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of 8-chloro-7-(2-propen-1-yl)-3-(4,4,4-trifluorobutyl)-3,7-dihydro-1H-purine-2,6-dione (1.0 g, 3.0 mmol) in DMF (15 ml) was treated with caesium carbonate (1.16 g, 3.6 mmol) and 3-bromo-1-propanol (0.3 ml, 3.3 mmol). The mixture was heated at 60° C. for 4 h and then cooled and evaporated. The residue was partitioned between EtOAc (50 ml) and water (50 ml). The organic phase was dried (MgSO4), filtered and evaporated. The product was purified by flash chromatography using a gradient elution from cyclohexane to EtOAc. Product-containing fractions were combined and evaporated to give the title compound as a colourless oil (0.82 g, 75%).

Workup

temperaturecooled
customevaporated
customThe residue was partitioned between EtOAc (50 ml) and water (50 ml)
dry with materialThe organic phase was dried (MgSO4)
filtrationfiltered
customevaporated
customThe product was purified by flash chromatography
washa gradient elution from cyclohexane to EtOAc
customevaporated

Sources & evidence

ORD record: ord-25feb408d3cd4f77addbaeeb92f4cebe
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08143264B2

Linked notes

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