Triethylamine → HCID 67980730, compound

HRID 1427479Notes

Reaction equation

HRID 1427479 reaction equation
[CH:1]1([CH:7]([C:9]2[CH:10]=[N:11][C:12]([C:15]3[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=3)=[N:13][CH:14]=2)[OH:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C>ClCCl.CS(C)=O>[CH:1]1([C:7]([C:9]2[CH:14]=[N:13][C:12]([C:15]3[CH:16]=[CH:17][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:19][CH:20]=3)=[N:11][CH:10]=2)=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 68062009HCID 68062009, compound

Product 1

HCID 67980730HCID 67980730, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of (+/−)-cyclohexyl{2-[4-(trifluoromethyl)phenyl]pyrimidin-5-yl}methanol (0.440 g, 1.31 mmol) in dichloromethane (4.8 ml), dimethyl sulfoxide (3.7 ml) and triethylamine (0.911 ml, 6.54 mmol) was cooled to 0° C. Sulfur trioxide pyridine complex (0.625 g, 3.92 mmol) was added in portions and the mixture stirred at 0° C. for 1 hour then slowly raised to ambient temperature over 12 hours. The reaction was quenched with water and diluted with diethylether. The aqueous layer was extracted with diethylether and the combined organic layers were washed with brine. The combined organic extracts were dried over magnesium sulfate, filtered and concentrated in vacuo, affording a crude solid. This material was used without further purification.

Workup

  1. additionSulfur trioxide pyridine complex (0.625 g, 3.92 mmol) was added in portions
  2. temperaturethen slowly raised to ambient temperature over 12 hours
  3. customThe reaction was quenched with water
  4. additiondiluted with diethylether
  5. extractionThe aqueous layer was extracted with diethylether
  6. washthe combined organic layers were washed with brine
  7. dry with materialThe combined organic extracts were dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customaffording a crude solid
  11. customThis material was used without further purification

Sources & evidence

ORD record
ord-cc0bc52ca06147ce8c0eaa5befd40574
Source dataset
uspto-grants-2015_01
Patent number
US08933104B2

Reaction notes

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