Triphenylphosphine → HCID 86653947, compound

HRID 2088407Notes

Reaction equation

HRID 2088407 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]([C:8]2[CH:9]=[C:10]([CH2:14][OH:15])[CH:11]=[CH:12][CH:13]=2)=[N:6][CH:7]=1.[CH2:16]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])(C)C)[CH:17]=[CH2:18].[C:27]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C[CH:28]=1.C([O-])(=O)C.[K+]>CN(C=O)C.[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC>[OH:15][CH2:14][C:10]1[CH:9]=[C:8]([C:5]2[N:4]=[CH:3][C:2](/[CH:18]=[CH:17]/[CH2:16][NH:19][C:20](=[O:26])[O:21][CH2:22][CH2:25][CH2:27][CH3:28])=[CH:7][N:6]=2)[CH:13]=[CH:12][CH:11]=1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 517044Potassium AcetateHCID 4067274tert-butyl N-(prop-2-en-1-yl)carbamateHCID 59484879(3-(5-Bromopyrimidin-2-yl)phenyl)methanol

Product 1

HCID 86653947HCID 86653947, compound

Reagents, catalysts & solvents 2

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

812 mg (3.06 mmol) of [3-(5-bromopyrimidin-2-yl)phenyl]methanol and 722 mg (4.59 mmol) of tert-butyl N-allylcarbamate are suspended in 16 ml of DMF, and 160 mg (0.61 mmol) of triphenylphosphine, 1.8 g (4.6 mmol) of potassium acetate and 1.28 g (4.59 mmol) of tetra-n-butylammonium chloride are added. The reaction mixture is degassed and flushed with argon, and 137 mg (0.0.61 mmol) of palladium(II) acetate are added under an argon atmosphere. The mixture is heated at 80° C. for 2 h. After cooling, the mixture is filtered off through kieselguhr with suction, and the filtrate is added to water and extracted with 2×100 ml of ethyl acetate, dried over sodium sulfate and evaporated. The product was reacted further without further purification. Yield: 380 mg; HPLC: Rt.=2.66 min (method A); LC-MS: 342 (M+H).

Workup

  1. customThe reaction mixture is degassed
  2. customflushed with argon, and 137 mg (0.0.61 mmol) of palladium(II) acetate
  3. additionare added under an argon atmosphere
  4. temperatureAfter cooling
  5. filtrationthe mixture is filtered off through kieselguhr with suction
  6. additionthe filtrate is added to water
  7. extractionextracted with 2×100 ml of ethyl acetate
  8. dry with materialdried over sodium sulfate
  9. customevaporated
  10. customThe product was reacted further without further purification
  11. custom=2.66 min (method A)

Sources & evidence

ORD record
ord-6dfc445f7f104cef96233cf8cb95dda8
Source dataset
uspto-grants-2013_05
Patent number
US08435986B2

Reaction notes

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