Triphenylphosphine → HCID 66706064, compound

HRID 1182823Notes

Reaction equation

HRID 1182823 reaction equation
[CH2:1]([C:5]1[N:6]=[C:7]([CH3:34])[N:8]([C:27]2[N:32]=[CH:31][C:30]([OH:33])=[CH:29][N:28]=2)[C:9](=[O:26])[C:10]=1[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[C:19]([C:24]#[N:25])=[CH:20][CH:21]=[CH:22][CH:23]=2)=[CH:14][CH:13]=1)[CH2:2][CH2:3][CH3:4].[CH2:35]([C:37]1[CH:38]=[CH:39][C:40]([CH2:43][CH2:44]O)=[N:41][CH:42]=1)[CH3:36].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OC(N=NC(OCC)=O)=O)C>O.O1CCCC1>[CH2:1]([C:5]1[N:6]=[C:7]([CH3:34])[N:8]([C:27]2[N:32]=[CH:31][C:30]([O:33][CH2:44][CH2:43][C:40]3[CH:39]=[CH:38][C:37]([CH2:35][CH3:36])=[CH:42][N:41]=3)=[CH:29][N:28]=2)[C:9](=[O:26])[C:10]=1[CH2:11][C:12]1[CH:13]=[CH:14][C:15]([C:18]2[C:19]([C:24]#[N:25])=[CH:20][CH:21]=[CH:22][CH:23]=2)=[CH:16][CH:17]=1)[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 788945-Ethyl-2-pyridineethanolHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 58553813HCID 58553813, compound

Product 1

HCID 66706064HCID 66706064, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

4′-{[4-butyl-1-(5-hydroxypyrimidin-2-yl)-2-methyl-6-oxo-1,6-dihydropyrimidin-5-yl]methyl}biphenyl-2-carbonitrile (50 mg, 0.111 mmol), 2-(5-ethylpyridin-2-yl)ethanol (16.8 mg, 0.111 mmol) and triphenylphosphine (44 mg, 0.167 mmol) were dried for 3 hrs in vacuo, purged with argon, added tetrahydrofuran (1 mL) and diethyl azodicarboxylic acid (2.2 mol/L toluene solution, 76 μL, 0.167 mmol), and stirred at room temperature for 2 hrs. The reaction mixture was added water and extracted with ethyl acetate. The organic layer was combined, washed with water and brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The resulting residues were subjected to silica gel column chromatography (hexane/ethyl acetate) to obtain 4′-{[4-butyl-1-{5-[2-(5-ethylpyridin-2-yl)ethoxy]pyrimidin-2-yl}-2-methyl-6-oxo-1,6-dihydropyrimidin-5-yl}methyl]biphenyl-2-carbonitrile (49 mg, 76%).

Workup

  1. custompurged with argon
  2. extractionextracted with ethyl acetate
  3. washwashed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-eabaa2775d1d4f7f94cafaecf8a2530d
Source dataset
uspto-grants-2014_03
Patent number
US08664226B2

Reaction notes

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