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

HRID 873186Notes

Reaction equation

HRID 873186 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

HCID 712438273-(((5-Oxo-1,2,3,5-tetrahydroimidazo[1,2-c]pyrimidin-7-yl)oxy)methyl)benzonitrileYield 62.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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%)

Sources & evidence

ORD record
ord-c529647aa5704663a5cb117a65b5e3ba
Source dataset
uspto-grants-2015_03
Patent number
US08975400B2

Reaction notes

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