Cesium carbonate → 6-(3-(1,3-Dioxoisoindolin-2-yl)-2-(tritylthio)propyl)-1,3-dimethyl-5-(4-methylthiazol-2-yl)-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione

HRID 2201229Notes

Reaction equation

HRID 2201229 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:7][N:8]1[C:13]2=[CH:14][NH:15][C:16]([C:17]3[S:18][CH:19]=[C:20]([CH3:22])[N:21]=3)=[C:12]2[C:11](=[O:23])[N:10]([CH3:24])[C:9]1=[O:25].Br[CH2:27][CH:28]([S:41][C:42]([C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1)([C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[CH2:29][N:30]1[C:38](=[O:39])[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:31]1=[O:40]>CC(N(C)C)=O>[O:39]=[C:38]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:31](=[O:40])[N:30]1[CH2:29][CH:28]([S:41][C:42]([C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)([C:43]1[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=1)[C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1)[CH2:27][N:15]1[C:16]([C:17]2[S:18][CH:19]=[C:20]([CH3:22])[N:21]=2)=[C:12]2[C:13]([N:8]([CH3:7])[C:9](=[O:25])[N:10]([CH3:24])[C:11]2=[O:23])=[CH:14]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 867234652-(3-Bromo-2-(tritylthio)propyl) isoindoline-1,3-dioneHCID 1363483951,3-dimethyl-5-(4-methylthiazol-2-yl)-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione

Product 1

HCID 867234646-(3-(1,3-Dioxoisoindolin-2-yl)-2-(tritylthio)propyl)-1,3-dimethyl-5-(4-methylthiazol-2-yl)-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
55 °C

Procedure

Cesium carbonate (1.537 g, 4.72 mmol) was added to a solution of 1,3-dimethyl-5-(4-methylthiazol-2-yl)-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione (Intermediate Nd) (0.652 g, 2.359 mmol) and 2-(3-bromo-2-(tritylthio)propyl) isoindoline-1,3-dione (2.011 g, 2.59 mmol) in dimethylacetamide (10 ml) and the mixture was stirred at 55° C. for 16 hours. The mixture was cooled to room temperature, partitioned between water (150 ml) and ethyl acetate (150 ml). The organic layer was separated, washed with brine (150 ml), dried over magnesium sulfate and evaporated under vacuum. Purification by chromatography on silica, eluting with 0-75% EtOAc/hexane afforded the title compound.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. custompartitioned between water (150 ml) and ethyl acetate (150 ml)
  3. customThe organic layer was separated
  4. washwashed with brine (150 ml)
  5. dry with materialdried over magnesium sulfate
  6. customevaporated under vacuum
  7. customPurification by chromatography on silica
  8. washeluting with 0-75% EtOAc/hexane

Sources & evidence

ORD record
ord-d47053379a89412387da2ea31c598a5b
Source dataset
uspto-grants-2016_06
Patent number
US09359381B2

Reaction notes

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