tert-Butanol → Ethyl 3-(6-(((tert-butyldiphenylsilyl)oxy)methyl)pyrimidin-4-yl)-3-cyclopropylpropanoate

HRID 1049495Notes

Reaction equation

HRID 1049495 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(C)([O-])C.[Na+].[Si:53]([O:70][CH2:71][C:72]1[N:77]=[CH:76][N:75]=[C:74]([C:78]([CH:85]2[CH2:87][CH2:86]2)=[CH:79][C:80]([O:82][CH2:83][CH3:84])=[O:81])[CH:73]=1)([C:66]([CH3:69])([CH3:68])[CH3:67])([C:60]1[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1)[C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1.C(O)(C)(C)C>C1(C)C=CC=CC=1.[Cu]Cl.CO>[Si:53]([O:70][CH2:71][C:72]1[N:77]=[CH:76][N:75]=[C:74]([CH:78]([CH:85]2[CH2:87][CH2:86]2)[CH2:79][C:80]([O:82][CH2:83][CH3:84])=[O:81])[CH:73]=1)([C:66]([CH3:67])([CH3:68])[CH3:69])([C:54]1[CH:55]=[CH:56][CH:57]=[CH:58][CH:59]=1)[C:60]1[CH:61]=[CH:62][CH:63]=[CH:64][CH:65]=1

Participants

8

Reactant 4

HCID 6386tert-ButanolHCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxideHCID 131736019Ethyl 3-(6-(((tert-butyldiphenylsilyl)oxy)methyl)pyrimidin-4-yl)-3-cyclopropylacrylate

Product 1

HCID 131736020Ethyl 3-(6-(((tert-butyldiphenylsilyl)oxy)methyl)pyrimidin-4-yl)-3-cyclopropylpropanoateYield 101.1%

Reagents, catalysts & solvents 3

HCID 62652Cuprous chlorideCatalystHCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

Under an argon atmosphere, to a solution of 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (844 mg) in toluene (50 mL) were added copper (I) chloride (134 mg) and sodium tert-butoxide (130 mg), and the mixture was stirred at room temperature for 5 min. To the obtained yellow suspension were successively added ethyl 3-(6-(((tert-butyldiphenylsilyl)oxy)methyl)pyrimidin-4-yl)-3-cyclopropylacrylate (6.60 g), polymethylhydrosiloxane (8.10 mL) and tert-butyl alcohol (2.56 mL) at room temperature, and the mixture was directly stirred for 7 hr. To the reaction mixture was added methanol, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (6.70 g) as a pale-yellow oil.

Workup

  1. customat room temperature
  2. stirringthe mixture was directly stirred for 7 hr
  3. customthe solvent was evaporated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-d66b1adbc3cb4e8eaea67974b163848a
Source dataset
uspto-grants-2016_07
Patent number
US09382188B2

Reaction notes

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