Tetrahydrofuran → HCID 86686212, compound

HRID 1021242Notes

Reaction equation

HRID 1021242 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[CH2:5][O:6][Si:7]([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8].C1COCC1.C([Li])CCC.CCCCCC.[N:33]1([C:39]2[N:44]=[CH:43][C:42]([CH:45]=[O:46])=[CH:41][N:40]=2)[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1>CCOC(C)=O.O>[Si:7]([O:6][CH2:5][C:4]1[CH:3]=[C:2]([CH:45]([C:42]2[CH:43]=[N:44][C:39]([N:33]3[CH2:34][CH2:35][O:36][CH2:37][CH2:38]3)=[N:40][CH:41]=2)[OH:46])[CH:16]=[CH:15][CH:14]=1)([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 31609782-(Morpholin-4-yl)pyrimidine-5-carbaldehydeHCID 220331471-Bromo-3-((((1,1-dimethylethyl)dimethylsilyl)oxy)methyl)benzeneHCID 178418244HCID 178418244, compound

Product 1

HCID 86686212HCID 86686212, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-78 °C

Procedure

[(3-Bromobenzyl)oxy](tert-butyl)dimethylsilane (860 mg) was mixed with THF (10 ml), followed by cooling to −78° C. under argon atmosphere. A 1.60 M n-butyl lithium/hexane solution (1.8 ml) was added dropwise thereto, followed by stirring at −78° C. for 10 minutes, and then 2-morpholin-4-ylpyrimidine-5-carboaldehyde (500 mg) was added thereto. The mixture was warmed to 0° C. over 1 hour and then stirred again at 0° C. for 1 hour. Water and EtOAc were added to the reaction mixture, and the organic layer was dried over Na2SO4 and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/EtOAc) to obtain [3-({[tert-butyl(dimethyl)silyl]oxy}methyl)phenyl][2-(morpholin-4-yl)pyrimidin-5-yl]methanol (914 mg).

Workup

  1. temperatureThe mixture was warmed to 0° C. over 1 hour
  2. stirringstirred again at 0° C. for 1 hour
  3. dry with materialthe organic layer was dried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (hexane/EtOAc)

Sources & evidence

ORD record
ord-d1602688f92f4cfea67bb4f975b75015
Source dataset
uspto-grants-2014_05
Patent number
US08716470B2

Reaction notes

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