Trifluoroacetic acid → 3-(((5-Oxo-1,2,3,5-tetrahydroimidazo[1,2-c]pyrimidin-7-yl)oxy)methyl)benzonitrile

HRID 873186Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 873186
[C:1]([C:3]1[CH:4]=[C:5]([CH:25]=[CH:26][CH:27]=1)[CH2:6][O:7][C:8]1[CH:9]=[C:10]2[N:17](C(OC(C)(C)C)=O)[CH2:16][CH2:15][N:11]2[C:12](=[O:14])[N:13]=1)#[N:2].C(O)(C(F)(F)F)=O>ClCCl>[O:14]=[C:12]1[N:11]2[CH2:15][CH2:16][NH:17][C:10]2=[CH:9][C:8]([O:7][CH2:6][C:5]2[CH:4]=[C:3]([CH:27]=[CH:26][CH:25]=2)[C:1]#[N:2])=[N:13]1

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 71241009tert-butyl 7-((3-cyanobenzyl)oxy)-5-oxo-2,3-dihydroimidazo[1,2-c]pyrimidine-1(5H)-carboxylate

Produkt 1

HCID 712438273-(((5-Oxo-1,2,3,5-tetrahydroimidazo[1,2-c]pyrimidin-7-yl)oxy)methyl)benzonitrileAusbeute 62,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of tert-butyl 7-((3-cyanobenzyl)oxy)-5-oxo-2,3-dihydroimidazo[1,2-c]pyrim-idine-1(5H)-carboxylate (20 mg, 0.054 mmol) in dichloromethane (DCM) (4 mL) was added TFA (0.5 mL, 6.49 mmol) at room temperature. The reaction mixture was stirred at rt overnight, then concentrated to remove solvent, diluted with sat. NaHCO3 (5 mL) solution and EtOAc (15 mL). Separated organic part was dried over Na2SO4, filtered and concentrated. Purification via MDAP (Gilson GX-281, mobile phase: 0.01% NH4HCO3, CH3CN/water, 50˜95%) afforded the title product (9 mg) as a white solid.

Aufarbeitung

  1. concentrationconcentrated
  2. customto remove solvent
  3. additiondiluted with sat. NaHCO3 (5 mL) solution and EtOAc (15 mL)
  4. dry with materialSeparated organic part was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification via MDAP (Gilson GX-281, mobile phase: 0.01% NH4HCO3, CH3CN/water, 50˜95%)

Quellen und Nachweise

ORD-Eintrag
ord-c529647aa5704663a5cb117a65b5e3ba
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08975400B2

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