Hydrogen chloride-ethyl acetate → HCID 86686221, compound

HRID 2171653Notes

Reaction equation

HRID 2171653 reaction equation
[Si]([O:8][CH2:9][C:10]1[C:11]([F:35])=[C:12]([C:16]2[CH:17]=[N:18][C:19]([CH:22]3[CH2:27][CH2:26][N:25](C(OC(C)(C)C)=O)[CH2:24][CH2:23]3)=[N:20][CH:21]=2)[CH:13]=[CH:14][CH:15]=1)(C(C)(C)C)(C)C.Cl.CCOC(C)=O>CO>[F:35][C:11]1[C:12]([C:16]2[CH:17]=[N:18][C:19]([CH:22]3[CH2:23][CH2:24][NH:25][CH2:26][CH2:27]3)=[N:20][CH:21]=2)=[CH:13][CH:14]=[CH:15][C:10]=1[CH2:9][OH:8]

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 86686222HCID 86686222, compound

Product 1

HCID 86686221HCID 86686221, compoundYield 98.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

tert-Butyl 4-{5-[3-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-fluorophenyl]pyrimidin-2-yl}piperidin e-1-carboxylate (170 mg) was mixed with MeOH (1.7 ml), and a 4M hydrogen chloride/EtOAc (0.17 ml) was added thereto, followed by stirring at room temperature overnight. The reaction mixture was concentrated under reduced pressure, and 10% MeOH/CHCl3 and a saturated aqueous sodium hydrogen carbonate solution were added to the residue. Then, the reaction mixture was concentrated under reduced pressure. 10% MeOH/CHCl3 was added to the obtained residue, followed by stirring for 30 minutes. The filtrate was concentrated under reduced pressure to obtain {2-fluoro-3-[2-(piperidin-4-yl)pyrimidin-5-yl]phenyl}methanol (96 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, and 10% MeOH/CHCl3
  2. additiona saturated aqueous sodium hydrogen carbonate solution were added to the residue
  3. concentrationThen, the reaction mixture was concentrated under reduced pressure
  4. addition10% MeOH/CHCl3 was added to the obtained residue
  5. stirringby stirring for 30 minutes
  6. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-98bcee64e98d4d33928566b4a9097a9d
Source dataset
uspto-grants-2015_06
Patent number
US09051283B2

Reaction notes

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