Hydrochloric Acid → HCID 135592794, compound

HRID 2227249Notes

Reaction equation

HRID 2227249 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][N:8]2[C:11]2[C:16]([NH2:17])=[C:15]([C:18](=O)[CH2:19]C)[N:14]=[CH:13][N:12]=2)=[CH:4][CH:3]=1.Cl.C([OH:25])C>[Pd]>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][N:8]2[C:11]2[C:16]3[NH:17][C:19]([OH:25])=[CH:18][C:15]=3[N:14]=[CH:13][N:12]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 69963857HCID 69963857, compound

Product 1

HCID 135592794HCID 135592794, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To a solution of 4(6Chloro-2,3-dihydro-indol-1-yl)-5-amino-6-methylacetyl-pyrimidine (541 mg, 1.55 mmol) in 40 mL of ethanol was added 25 mol % of 10% palladium on carbon (125 mg) and 0.11 mL of 1N HCl (1.55 mmol). The mixture was hydrogenated for 3 hours at 3.4 atm (50 psi)(H2). The reaction is filtered through Celite® and concentrated in vacuo. The brown residue was slurried in methanol and the white solid was filtered off (279 mg, 63%): LC-MS: 287 (M+); anal. RP18-HPLC RT: 5.61 minutes; MP: 250° C. (dec).

Workup

  1. filtrationThe reaction is filtered through Celite®
  2. concentrationconcentrated in vacuo
  3. filtrationthe white solid was filtered off (279 mg, 63%)

Sources & evidence

ORD record
ord-f6e86b98be72427983596a812fbcc7a7
Source dataset
uspto-grants-2002_07
Patent number
US06413971B1

Reaction notes

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