Hydrochloric Acid → HCID 21075875, compound

HRID 1374154Notes

Reaction equation

HRID 1374154 reaction equation
[C:1]([C:3]1[N:8]=[CH:7][C:6]([C:9]2[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[C:10]=2[C:11]([O:13][CH3:14])=[O:12])=[CH:5][N:4]=1)#[N:2].[ClH:20].[H][H]>CO.[Pd]>[ClH:20].[NH2:2][CH2:1][C:3]1[N:4]=[CH:5][C:6]([C:9]2[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[C:10]=2[C:11]([O:13][CH3:14])=[O:12])=[CH:7][N:8]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 21075877HCID 21075877, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21075875HCID 21075875, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Methyl 2-(2-cyanopyrimidin-5-yl)-6-fluorobenzoate (100 mg, 0.389 mmol) was dissolved in methanol (4.0 mL) under nitrogen. Palladium on carbon (840 mg, 10% wt/wt) and concentrated HCl (32 μL) were then added prior to exchanging the nitrogen for hydrogen. After 30 minutes the reaction was judged complete (LCMS). The reaction mixture was filtered through celite and the celite was washed with additional methanol. Removal of the solvent under reduced pressure provided methyl 2-[2-(aminomethyl)pyrimidin-5-yl]-6-fluorobenzoate hydrochloride (104 mg) of 90% pure material, as determined by proton NMR and LCMS.

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. washthe celite was washed with additional methanol
  3. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-f0a8febb8d1d480cbc3fbd80f5eb16db
Source dataset
uspto-grants-2007_01
Patent number
US07163951B2

Reaction notes

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