Isobutylene oxide → HCID 59258915, compound

HRID 472239Notes

Reaction equation

HRID 472239 reaction equation
[CH:1]1([N:6]2[C:11]3[N:12]=[C:13]([S:17][CH3:18])[N:14]=[C:15]([CH3:16])[C:10]=3[CH:9]=[C:8]([C:19]3[CH:20]=[N:21][NH:22][CH:23]=3)[C:7]2=[O:24])[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:25][C:26]1([CH3:29])[CH2:28][O:27]1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[CH:1]1([N:6]2[C:11]3[N:12]=[C:13]([S:17][CH3:18])[N:14]=[C:15]([CH3:16])[C:10]=3[CH:9]=[C:8]([C:19]3[CH:20]=[N:21][N:22]([CH2:25][C:26]([OH:27])([CH3:29])[CH3:28])[CH:23]=3)[C:7]2=[O:24])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 11208Isobutylene oxideHCID 11430Potassium CarbonateHCID 67237870HCID 67237870, compound

Product 1

HCID 59258915HCID 59258915, compoundYield 12%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To the solution of 8-Cyclopentyl-4-methyl-2-methylsulfanyl-6-(1H-pyrazol-4-yl)-8H-pyrido[2,3-d]pyrimidin-7-one (100 mg, 0.29 mmol) in 5 ml of DMSO were added 2,2-Dimethyl-oxirane (0.03 ml, 1.20 eq.), and potassium carbonate (40.5 mg, 1.00 eq.) under nitrogen. The reaction mixture was stirred at room temperature. After two hours, no reaction. The reaction mixture was heated to 100° C. for 30 min. Some product was formed. It was continued heating for 1 hour. Starting material was gone. The reaction mixture was partitioned in EA/brine. EA layer was dried and concentrated. It was further purified by chromatography (10% MeOH/DCM). 15 mg of product was obtained at yield of 12%.

Workup

  1. customno reaction
  2. temperatureThe reaction mixture was heated to 100° C. for 30 min
  3. customSome product was formed
  4. temperatureIt was continued heating for 1 hour
  5. customThe reaction mixture was partitioned in EA/brine
  6. dry with materialEA layer was dried
  7. concentrationconcentrated
  8. customIt was further purified by chromatography (10% MeOH/DCM)

Sources & evidence

ORD record
ord-0a5355dd35604ffb89c186e87166e80c
Source dataset
uspto-grants-2014_01
Patent number
US08633204B2

Reaction notes

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