Triphenylphosphine → 3-[3,5-Difluoro-4-(2-isopropylsulfanyl-pyrimidin-4-ylmethoxy)phenyl]-propionic acid ethyl ester

HRID 62936Notes

Reaction equation

HRID 62936 reaction equation
[CH:1]([S:4][C:5]1[N:10]=[C:9]([CH2:11][OH:12])[CH:8]=[CH:7][N:6]=1)([CH3:3])[CH3:2].[CH2:13]([O:15][C:16](=[O:28])[CH2:17][CH2:18][C:19]1[CH:24]=[C:23]([F:25])[C:22](O)=[C:21]([F:27])[CH:20]=1)[CH3:14].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[CH2:13]([O:15][C:16](=[O:28])[CH2:17][CH2:18][C:19]1[CH:24]=[C:23]([F:25])[C:22]([O:12][CH2:11][C:9]2[CH:8]=[CH:7][N:6]=[C:5]([S:4][CH:1]([CH3:3])[CH3:2])[N:10]=2)=[C:21]([F:27])[CH:20]=1)[CH3:14]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 23136305Ethyl 3-(3,5-difluoro-4-hydroxyphenyl)propanoateHCID 90118246(2-Isopropylsulfanyl-pyrimidin-4-yl)-methanol

Product 1

HCID 901184523-[3,5-Difluoro-4-(2-isopropylsulfanyl-pyrimidin-4-ylmethoxy)phenyl]-propionic acid ethyl esterYield 82.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(2-Isopropylsulfanyl-pyrimidin-4-yl)-methanol (0.08 g, 0.43 mmol) obtained in Step C of Preparation Example 24, 3-(3,5-difluoro-4-hydroxy-phenyl)-propionic acid ethyl ester (0.1 g, 0.43 mmol) obtained in Step D of Preparation Example 2 and triphenyl phosphine (0.114 g, 0.43 mmol) were dissolved in anhydrous THF (3 mL), and the mixture was stirred at room temperature for 10 minutes. Diisopropyl azodicarboxylate (0.085 mL, 0.43 mmol) was added slowly thereto. The mixture was stirred at room temperature for 18 hours, concentrated under reduced pressure, and separated by column chromatography (eluent: 100% DCM) to obtain the title compound (0.14 g, 81%).

Workup

  1. stirringThe mixture was stirred at room temperature for 18 hours
  2. concentrationconcentrated under reduced pressure
  3. customseparated by column chromatography (eluent: 100% DCM)

Sources & evidence

ORD record
ord-51b33dac48314a61aef22e2df7ae2823
Source dataset
uspto-grants-2016_09
Patent number
US09447044B2

Reaction notes

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