Tetrahydrofuran → [3-(2-Ethoxypyrimidin-5-yl)-2-fluorophenyl]methanol

HRID 2171675Notes

Reaction equation

HRID 2171675 reaction equation
[Si]([O:8][CH2:9][C:10]1[C:11]([F:23])=[C:12]([C:16]2[CH:17]=[N:18][C:19](Cl)=[N:20][CH:21]=2)[CH:13]=[CH:14][CH:15]=1)(C(C)(C)C)(C)C.C1C[O:27][CH2:26][CH2:25]1.[O-]CC.[Na+].CCCC[N+](CCCC)(CCCC)CCCC.[F-].C1COCC1>CCOC(C)=O.O>[CH2:26]([O:27][C:19]1[N:20]=[CH:21][C:16]([C:12]2[C:11]([F:23])=[C:10]([CH2:9][OH:8])[CH:15]=[CH:14][CH:13]=2)=[CH:17][N:18]=1)[CH3:25]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 2723922Sodium ethoxideHCID 11078149TBAF tetrahydrofuranHCID 866862315-[3-({[tert-Butyl(dimethyl)silyl]oxy}methyl)-2-fluorophenyl]-2-chloropyrimidine

Product 1

HCID 68309615[3-(2-Ethoxypyrimidin-5-yl)-2-fluorophenyl]methanol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

5-[3-({[tert-Butyl(dimethyl)silyl]oxy}methyl)-2-fluorophenyl]-2-chloropyrimidine (200 mg) was mixed with THF (4 ml), and sodium ethoxide (132 mg) was added thereto, followed by stirring at room temperature for 3 hours, and then a 1M TBAF/THF solution (1.2 ml) was added thereto, followed by stirring at room temperature for 1 hour. Water and EtOAc were added to the reaction mixture, and the organic layer was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/EtOAc) to obtain [3-(2-ethoxypyrimidin-5-yl)-2-fluorophenyl]methanol (129 mg).

Workup

  1. additionwas added
  2. stirringby stirring at room temperature for 1 hour
  3. concentrationthe organic layer was concentrated under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography (hexane/EtOAc)

Sources & evidence

ORD record
ord-4191e15b9575427db1e949789d5c502c
Source dataset
uspto-grants-2015_06
Patent number
US09051283B2

Reaction notes

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