Trifluoroacetic acid → (R)-2-(4-(3-aminopyrrolidin-1-yl)-7-methylquinazolin-2-yl)phenol

HRID 1693019Notes

Reaction equation

HRID 1693019 reaction equation
C(OC(=O)[NH:7][C@@H:8]1[CH2:12][CH2:11][N:10]([C:13]2[C:22]3[C:17](=[CH:18][C:19]([CH3:23])=[CH:20][CH:21]=3)[N:16]=[C:15]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[OH:30])[N:14]=2)[CH2:9]1)(C)(C)C.C(O)(C(F)(F)F)=O>C([O-])(O)=O.[Na+].C(Cl)Cl>[NH2:7][C@@H:8]1[CH2:12][CH2:11][N:10]([C:13]2[C:22]3[C:17](=[CH:18][C:19]([CH3:23])=[CH:20][CH:21]=3)[N:16]=[C:15]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[OH:30])[N:14]=2)[CH2:9]1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 136121326tert-butyl(R)-1-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)pyrrolidin-3-ylcarbamate

Product 1

HCID 136121376(R)-2-(4-(3-aminopyrrolidin-1-yl)-7-methylquinazolin-2-yl)phenol

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

To (R)-{1-[2-(2-hydroxy-phenyl)-7-methyl-quinazolin-4-yl]-pyrrolidin-3-yl}-carbamic acid tert-butyl ester (1.54 g, 3.67 mmol) at room temperature was added 10 mL of a 1:1 TFA:CH2Cl2 solution. The reaction mixture was stirred for 30 min and diluted with 10 mL of saturated NaHCO3 and 15 mL of CH2Cl2. The resulting emulsion was filtered, and the organic layer was separated and dried over Na2SO4. The solvent was removed under reduced pressure to give (R)-2-[4-(3-amino-pyrrolidin-1-yl)-7-methyl-quinazolin-2-yl]-phenol. LC/MS: m/z 321.2 (M+H)+ at 1.91 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

  1. filtrationThe resulting emulsion was filtered
  2. customthe organic layer was separated
  3. dry with materialdried over Na2SO4
  4. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-6156787f72b74507a5a8882ad664e6e0
Source dataset
uspto-grants-2012_04
Patent number
US08158637B2

Reaction notes

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