Triphenylphosphine → HCID 178481544, compound

HRID 1468788Notes

Reaction equation

HRID 1468788 reaction equation
C([SiH2][O:6][C:7](C)(C)[C:8]1[CH:13]=[CH:12][C:11]([C@@H:14]2[CH2:19][CH2:18][C@H:17]([OH:20])[CH2:16][CH2:15]2)=[CH:10][CH:9]=1)(C)(C)C.O[C:24]1[N:25]([CH3:37])[C:26](=[O:36])[CH:27]=[C:28]([C:30]2[CH:35]=[CH:34][N:33]=[CH:32][N:31]=2)[N:29]=1.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.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Cl-].[NH4+]>O1CCCC1>[OH:6][CH2:7][C:8]1[CH:9]=[CH:10][C:11]([C@H:14]2[CH2:15][CH2:16][C@H:17]([O:20][C:24]3[N:25]([CH3:37])[C:26](=[O:36])[CH:27]=[C:28]([C:30]4[CH:35]=[CH:34][N:33]=[CH:32][N:31]=4)[N:29]=3)[CH2:18][CH2:19]2)=[CH:12][CH:13]=1

Participants

8

Reactant 6

HCID 11776TriphenylphosphineHCID 25517Ammonium ChlorideHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 2724141Tetrabutylammonium FluorideHCID 178455428HCID 178455428, compoundHCID 178481605HCID 178481605, compound

Product 1

HCID 178481544HCID 178481544, compoundYield 33.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of cis-4-[4-(tert-butyl-dimethyl-silanyloxymethyl)phenyl]cyclohexanol (600 mg, 1.87 mmol), 2-hydroxy-1-methyl-1H-[4,4′]bipyrimidinyl-6-one (382 mg, 1.87 mmol), triphenylphosphine (540 mg, 2.06 mmol) in tetrahydrofuran (6.2 ml) was added diisopropyl azodicarboxylate (40 wt % in toluene, 1.04 g, 2.06 mmol) under nitrogen atmosphere. The mixture was stirred at room temperature overnight. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent; hexane/ethyl acetate=60/40 to 50/50) to afford a colorless solid. This compound was dissolved into tetrahydrofuran (7.5 ml) and cooled to 0° C. Tetrabutylammonium fluoride (1.0M in tetrahydrofuran, 3.0 ml, 3.0 mmol) was added to the solution. The mixture was warmed to room temperature and stirred for one hour. The mixture was poured into saturated aqueous ammonium chloride solution, and extracted with dichloromethane. The organic layer was dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography (eluent; ethyl acetate) to afford 2-[trans-4-(4-hydroxymethyl-phenyl)cyclohexyloxy]-1-methyl-1H-[4,4′]bipyrimidinyl-6-one as a colorless solid (243 mg, 0.619 mmol, 33%).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue was purified by silica gel column chromatography (eluent; hexane/ethyl acetate=60/40 to 50/50)
  3. customto afford a colorless solid
  4. temperaturecooled to 0° C
  5. temperatureThe mixture was warmed to room temperature
  6. stirringstirred for one hour
  7. extractionextracted with dichloromethane
  8. dry with materialThe organic layer was dried over sodium sulfate
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified by silica gel column chromatography (eluent; ethyl acetate)

Sources & evidence

ORD record
ord-796aeeafcca74f618ba98a887fac21db
Source dataset
uspto-grants-2015_04
Patent number
US09006232B2

Reaction notes

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