Diethyl Sulfate → HCID 178467887, compound

HRID 1530791Notes

Reaction equation

HRID 1530791 reaction equation
[Cl:1][C:2]1[C:3]([NH:10][C@H:11]2[CH2:16][CH2:15][C@@H:14]([CH:17]([OH:22])[C:18]([F:21])([F:20])[F:19])[CH2:13][CH2:12]2)=[N:4][CH:5]=[N:6][C:7]=1[CH2:8][CH3:9].[H-].[Na+].[H][H].S(OCC)(O[CH2:31][CH3:32])(=O)=O>O1CCCC1.CO>[Cl:1][C:2]1[C:3]([NH:10][C@H:11]2[CH2:12][CH2:13][C@@H:14]([CH:17]([O:22][CH2:31][CH3:32])[C:18]([F:19])([F:20])[F:21])[CH2:15][CH2:16]2)=[N:4][CH:5]=[N:6][C:7]=1[CH2:8][CH3:9]

Participants

7

Reactant 4

HCID 6163Diethyl SulfateHCID 24758Sodium hydrideHCID 178418361HCID 178418361, compoundHCID 178437736HCID 178437736, compound

Product 1

HCID 178467887HCID 178467887, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

0.61 g of 5-chloro-6-ethyl-4-[cis-4-(1-hydroxy-2,2,2-trifluoroethyl)cyclohexylamino]pyrimidine were added to a suspension of 0.08 g of sodium hydride (80% dispersion in oil) in 10 ml of tetrahydrofuran, and the mixture was stirred at 50° C. until the evolution of hydrogen had ended. 0.28 g of diethyl sulfate were added, and the mixture was heated under reflux for 4 hours. The mixture was cooled to room temperature and a small amount of methanol was added dropwise to destroy excess sodium hydride, the mixture was concentrated and the residue was taken up in dilute ammonia solution and dichloromethane. The organic phase was dried and concentrated. Purification was carried out by silica gel chromatography (petroleum ether/ethyl acetate 1:1). to give the title product as a colourless oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 4 hours
  3. customto destroy excess sodium hydride
  4. concentrationthe mixture was concentrated
  5. customThe organic phase was dried
  6. concentrationconcentrated
  7. customPurification

Sources & evidence

ORD record
ord-9120325dddb64e30b2591cb23b6cffc6
Source dataset
uspto-grants-2001_03
Patent number
US06197729B1

Reaction notes

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