Triphenylphosphine → HCID 86719330, compound

HRID 1752821Notes

Reaction equation

HRID 1752821 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]2[N:9]=[C:10]([S:12][CH2:13][CH2:14][OH:15])[N:11]=[C:4]2[N:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[C:36]1[CH:41]=[CH:40][N:39]=[CH:38][CH:37]=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O.O1CCCC1>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]2[N:9]=[C:10]([S:12][CH2:13][CH2:14][O:15][C:36]3[CH:41]=[CH:40][N:39]=[CH:38][CH:37]=3)[N:11]=[C:4]2[N:3]=1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 8179216HCID 8179216, compoundHCID 178418642HCID 178418642, compound

Product 1

HCID 86719330HCID 86719330, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-({5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl}sulfanyl)ethan-1-ol (100 mg, 0.446 mmol), triphenylphosphine (175 mg, 0.670 mmol), 4-hydroxypyridine (55 mg, 0.58 mmol), and tetrahydrofuran (0.5 mL) was added to a 20 mL scintillation vial. The mixture was placed in a sonicating bath, and diisopropyl azodicarboxylate (0.133 mL, 0.67 mmol) was added dropwise. Sonication was allowed to continue for 15 min, and progress of the reaction was monitored by HPLC with UV detection at 215 nm. Water (5 mL) was added to the mixture, stirred, and decanted. The oily residue was dissolved in 50 mL of ethyl acetate and extracted with 3 mL of 1 M aqueous HCl. The acidic layer was separated, and the pH was adjusted to basic with saturated aqueous sodium bicarbonate. The basic layer was extracted with 4 mL of ethyl acetate which was dried (Na2SO4), filtered, and concentrated under reduced pressure. The crude material was purified by silical gel chromatography using a gradient elution of 0-10% methanol in dichloromethane. The title compound was obtained as a white powder (0.025 g, 19% yield). EM (calc.): 301.1; MS (ESI) m/e: 302.1 (M+H)+. 1H NMR (DMSO-d6, 400 MHz) δ ppm: 8.38 (dd, 2H), 7.13 (s, 1H), 7.04 (dd, 2H), 4.43 (t, 2H), 3.62 (t, 2H), 2.67 (s, 3H), 2.55 (s, 3H).

Workup

  1. additionwas added to a 20 mL scintillation vial
  2. customThe mixture was placed in a sonicating bath
  3. customSonication
  4. customdecanted
  5. dissolutionThe oily residue was dissolved in 50 mL of ethyl acetate
  6. extractionextracted with 3 mL of 1 M aqueous HCl
  7. customThe acidic layer was separated
  8. extractionThe basic layer was extracted with 4 mL of ethyl acetate which
  9. dry with materialwas dried (Na2SO4)
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure
  12. customThe crude material was purified by silical gel chromatography
  13. washa gradient elution of 0-10% methanol in dichloromethane

Sources & evidence

ORD record
ord-f63049c2293448fdb6710cbe1054fe81
Source dataset
uspto-grants-2015_10
Patent number
US09163027B2

Reaction notes

Loading…