Dimethyl Sulfoxide → HCID 14513901, compound

HRID 1590079Notes

Reaction equation

HRID 1590079 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[F:11][C:12]1[CH:17]=[CH:16][C:15]([CH:18]2[C:23](=[CH:24][OH:25])[C:22]([CH:26]([CH3:28])[CH3:27])=[N:21][C:20]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[N:19]2)=[CH:14][CH:13]=1.C(Cl)Cl.C1COCC1>C(Cl)Cl.CCOCC.C(N(CC)CC)C>[F:11][C:12]1[CH:13]=[CH:14][C:15]([C:18]2[C:23]([CH:24]=[O:25])=[C:22]([CH:26]([CH3:28])[CH3:27])[N:21]=[C:20]([C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)[N:19]=2)=[CH:16][CH:17]=1

Participants

8

Reactant 4

HCID 679Dimethyl SulfoxideHCID 65578Oxalyl chlorideHCID 21919333Tetrahydrofurane dichloromethaneHCID 178440000HCID 178440000, compound

Product 1

HCID 14513901HCID 14513901, compoundYield 83%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
-78 °C

Procedure

Dimethylsulfoxide (DMSO) (3.10 gm, 39.7 mmol) was added to a solution of oxalyl chloride (2.520 gm, 19.8 mmol) in methylene chloride (100 ml) which was cooled to -78° C. under argon. The solution was allowed to stir 15 minutes. Then, 4-(4-fluorophenyl)-6-(1-methylethyl)-2-phenyl-5-hydroxymethylene-pyrimidine obtained in step (iii) above (4.942 gm, 15.3 mmol) was added to the flask as a methylene chloride/THF (25 ml/10 ml) solution. The solution was stirred for 20 minutes and then triethylamine (10.6 ml) was added. The solution was stirred for an additional 10 minutes, then was warmed to room temperature. The solution was diluted with ether, washed with water and brine, then dried over Na2SO4, filtered and concentrated to afford a yellow solid. The solid was recrystallized from EtOAc/hexane to give the title compound as fine yellow needles (4.064 gm, 83%) (mp: 127-129° C.).

Workup

  1. stirringThe solution was stirred for 20 minutes
  2. stirringThe solution was stirred for an additional 10 minutes
  3. temperaturewas warmed to room temperature
  4. washwashed with water and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto afford a yellow solid
  9. customThe solid was recrystallized from EtOAc/hexane

Sources & evidence

ORD record
ord-6066751ff8b549fdbaec7686d29586f0
Source dataset
uspto-grants-1993_04
Patent number
US05202327

Reaction notes

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