Potassium Carbonate → HCID 86723432, compound

HRID 2201189Notes

Reaction equation

HRID 2201189 reaction equation
Br[CH2:2][CH2:3][CH2:4][OH:5].[CH2:6]([O:13][C:14](=[O:35])[NH:15][N:16]1[C:24]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[C:23]2[C:18]([N:19]([CH3:34])[C:20](=[O:33])[N:21]([CH3:32])[C:22]2=[O:31])=[CH:17]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C([O-])([O-])=O.[K+].[K+]>[Cl-].C([N+](C)(C)C)C1C=CC=CC=1.C(#N)C.O>[CH2:6]([O:13][C:14](=[O:35])[N:15]([N:16]1[C:24]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[C:23]2[C:18]([N:19]([CH3:34])[C:20](=[O:33])[N:21]([CH3:32])[C:22]2=[O:31])=[CH:17]1)[CH2:2][CH2:3][CH2:4][OH:5])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 123083-Bromo-1-propanolHCID 86723431HCID 86723431, compound

Product 1

HCID 86723432HCID 86723432, compound

Reagents, catalysts & solvents 3

HCID 5963Benzyltrimethylammonium chlorideCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

3-Bromopropan-1-ol (0.645 ml, 7.14 mmol) was added to a suspension of (1,3-Dimethyl-2,4-dioxo-5-phenyl-1,2,3,4-tetrahydro-pyrrolo[3,4-d]pyrimidin-6-yl)-carbamic acid benzyl ester (step 1) (2.22 g, 5.49 mmol), K2CO3 (2.276 g, 16.47 mmol) and benzyltrimethylammonium chloride (0.102 g, 0.549 mmol) in acetonitrile (50 ml). The mixture was heated to 60° C. and stirred for 40 mins. The reaction mixture was cooled to RT and diluted with water. The mixture was extracted with EtOAc (2×) and the combined organic phases washed with brine, dried over sodium sulphate and evaporated under reduced pressure. Purification by chromatography on silica, eluting with EtOAc/hexane and then MeOH/EtOAc afforded the title compound as a white foam.

Workup

  1. temperatureThe reaction mixture was cooled to RT
  2. extractionThe mixture was extracted with EtOAc (2×)
  3. washthe combined organic phases washed with brine
  4. dry with materialdried over sodium sulphate
  5. customevaporated under reduced pressure
  6. customPurification by chromatography on silica
  7. washeluting with EtOAc/hexane

Sources & evidence

ORD record
ord-7039d0a674174c82b28ea5dc70ccb962
Source dataset
uspto-grants-2016_06
Patent number
US09359381B2

Reaction notes

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