Dimethyl Sulfate → HCID 131736982, compound

HRID 58185Notes

Reaction equation

HRID 58185 reaction equation
[C:1]([O:5][C:6]([N:8]([C:24]1[CH:29]=[CH:28][C:27]([CH2:30][OH:31])=[CH:26][C:25]=1[N+:32]([O-:34])=[O:33])[C:9]1[N:14]=[CH:13][N:12]=[C:11]([N:15]([CH3:23])[C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:35](=O)([O-])[O-].[K+].[K+].S(OC)(OC)(=O)=O>CC(C)=O>[C:1]([O:5][C:6]([N:8]([C:24]1[CH:29]=[CH:28][C:27]([CH2:30][O:31][CH3:35])=[CH:26][C:25]=1[N+:32]([O-:34])=[O:33])[C:9]1[N:14]=[CH:13][N:12]=[C:11]([N:15]([CH3:23])[C:16](=[O:22])[O:17][C:18]([CH3:20])([CH3:21])[CH3:19])[CH:10]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 131736981HCID 131736981, compound

Product 1

HCID 131736982HCID 131736982, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of tert-butyl (6-((tert-butoxycarbonyl)(4-(hydroxymethyl)-2-nitrophenyl)amino)pyrimidin-4-yl)(methyl)carbamate (1.5 g, 3.488 mmol) in acetone (20 mL) under an argon atmosphere at 0° C., was added potassium carbonate (0.48 g, 6.97 mmol) followed by dimethyl sulfate (0.87 g, 6.97 mmol). The resulting reaction mixture was then refluxed for 24 h and then allowed to cool to rt. The reaction mixture was concentrated under vacuum to obtain a crude residue. The residue was purified by silica gel column chromatography to afford the title compound (0.3 g, yield: 19%) as a solid. MS (ESI): 490.55 [M+H]+.

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas then refluxed for 24 h
  3. concentrationThe reaction mixture was concentrated under vacuum
  4. customto obtain a crude residue
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-48e3532d41394c3f97f034e26bd5c398
Source dataset
uspto-grants-2016_09
Patent number
US09434697B2

Reaction notes

Loading…