Diethyl Ether → HCID 10159028, compound

HRID 2181625Notes

Reaction equation

HRID 2181625 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:17]2[N:16]=[C:15]([CH2:18][CH3:19])[NH:14][C:13]=2[C:12](=[O:20])[N:11]([CH3:21])[CH2:10]1.C([O-])([O-])=O.[K+].[K+].CS([CH:32]([CH2:36][CH:37]=[CH2:38])[CH2:33][CH:34]=[CH2:35])(=O)=O.CCOCC>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:17]2[N:16]=[C:15]([CH2:18][CH3:19])[N:14]([CH:32]([CH2:36][CH:37]=[CH2:38])[CH2:33][CH:34]=[CH2:35])[C:13]=2[C:12](=[O:20])[N:11]([CH3:21])[CH2:10]1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 11430Potassium CarbonateHCID 11278790HCID 11278790, compoundHCID 22481840HCID 22481840, compound

Product 1

HCID 10159028HCID 10159028, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Prepared by the method described in example 8 using the appropriate starting materials except for part “B” to give the desired product. Part “B” was replaced with the following procedure. A solution of 3-(2,4-dichlorophenyl)-8-ethyl-1-methyl-1,2,3,7-tetrahydro-6H-purin-6-one (65 mg, 0.20 mmol) in anhydrous DMF (1.2 mL) was treated with finely ground K2CO3 (83 mg, 0.60 mmol). After stirring 5 min at rt, 4-methanesulfonyl-1,6-heptadiene (203 μL, 1.11 mmol) was added via syringe and the reaction mixture was heated at 90° C. for 4 h. The mixture was cooled to rt and transferred to a separatory funnel containing ether (50 mL). The organic layer was washed with water (4×15 mL), brine (15 mL), dried over MgSO4, filtered, and concentrated. Purification of the residue by prep plate (1000 μM silica gel plate, 25% ethyl acetate in hexanes) followed by further purification by reverse phase HPLC afforded the title compound (15 mg, 18% yield) as a colorless oil; HRMS (ESI) m/e 419.1435 [(M+H)+, calcd for C21H25N4OCl2 419.1405].

Workup

  1. temperaturethe reaction mixture was heated at 90° C. for 4 h
  2. temperatureThe mixture was cooled to rt
  3. customtransferred to a separatory funnel
  4. washThe organic layer was washed with water (4×15 mL), brine (15 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification of the residue by prep plate (1000 μM silica gel plate, 25% ethyl acetate in hexanes)
  9. customfollowed by further purification by reverse phase HPLC

Sources & evidence

ORD record
ord-2183a748f575463e8ac5b407cc2e1224
Source dataset
uspto-grants-2005_05
Patent number
US06894045B2

Reaction notes

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