Hydroquinone → HCID 178437723, compound

HRID 1458655Notes

Reaction equation

HRID 1458655 reaction equation
[C:1]([C@@H:5]1[CH2:10][CH2:9][C@H:8]([NH:11][C:12]2[C:17]([Cl:18])=[C:16]([CH:19](S(C)=O)[CH3:20])[N:15]=[CH:14][N:13]=2)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].C1(C=CC(O)=CC=1)O.O>COCCOCCOC>[C:1]([C@@H:5]1[CH2:10][CH2:9][C@H:8]([NH:11][C:12]2[C:17]([Cl:18])=[C:16]([CH:19]=[CH2:20])[N:15]=[CH:14][N:13]=2)[CH2:7][CH2:6]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 785HydroquinoneHCID 962WaterHCID 178437724HCID 178437724, compound

Product 1

HCID 178437723HCID 178437723, compound

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Conditions

Temperature
150 °C

Procedure

A solution of 7.6 g (21 mmol) of 4-(cis-4-tert-butylcyclohexylamino)-5-chloro-6-(1-methylsulfinylethyl)pyrimidine (Example 26) in 100 ml of diethylene glycol dimethyl ether to which a little hydroquinone had been added was heated at 150° C. for 30 minutes. After cooling to room temperature the mixture was poured into water and extracted by stirring with dichloromethane. This left a brown oil which was extracted twice by stirring with petroleum ether. The petroleum ether phase was concentrated and the residue was purified with chromatography on silica gel, to give 1.1 g (17.8% of theory) of colorless solid.

Workup

  1. temperatureAfter cooling to room temperature the mixture
  2. extractionextracted
  3. waitThis left a brown oil which
  4. extractionwas extracted twice
  5. stirringby stirring with petroleum ether
  6. concentrationThe petroleum ether phase was concentrated
  7. customthe residue was purified with chromatography on silica gel
  8. customto give 1.1 g (17.8% of theory) of colorless solid

Sources & evidence

ORD record
ord-195785ee46db4a3a9f2c9fe6ccd12a39
Source dataset
uspto-grants-1998_12
Patent number
US05852023

Reaction notes

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