Hydrochloric Acid → HCID 18617786, compound

HRID 1264316Notes

Reaction equation

HRID 1264316 reaction equation
[CH3:1][N:2]([CH3:18])[C:3]1[N:8]=[C:7]([C:9]2[CH:17]=[CH:16][C:12]([C:13]([OH:15])=[O:14])=[CH:11][CH:10]=2)[CH:6]=[CH:5][N:4]=1.Cl>O.[Pd]>[CH3:1][N:2]([CH3:18])[C:3]1[NH:8][CH:7]([C:9]2[CH:17]=[CH:16][C:12]([C:13]([OH:15])=[O:14])=[CH:11][CH:10]=2)[CH2:6][CH2:5][N:4]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 18617838HCID 18617838, compound

Product 1

HCID 18617786HCID 18617786, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

To a solution of 4-(2-dimethylamino-pyrimidin-4-yl)-benzoic acid (275 mg, 1.13 mmol reference example 92aab) in H2O (13 ml) was added conc HCl (212 μL, 2.54 mmol) followed by 10% palladium on carbon (366 mg). The resulting mixture was stirred under H2 for 2.5 hrs. The mixture was filtered through a celite pad to remove the catalyst, using CH2Cl2 as a wash. The filtrate was concentrated under reduced pressure to give 260 mg of product as the HCl salt. MS (ion spray) m/z 248 (M+H)+.

Workup

  1. filtrationThe mixture was filtered through a celite pad
  2. customto remove the catalyst
  3. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-4b7f91949108487899b650eefcf7599d
Source dataset
uspto-grants-2003_04
Patent number
US06541505B1

Reaction notes

Loading…