Hydrochloric Acid → HCID 57497103, compound

HRID 2409187Notes

Reaction equation

HRID 2409187 reaction equation
[NH2:1][C:2]1[N:7]([CH3:8])[C:6](=[O:9])[C:5]([CH3:11])([CH3:10])[C@:4]([C:13]2[CH:18]=[C:17]([NH:19][C:20]3[N:24](CC4C=CC=CC=4)[N:23]=[CH:22][CH:21]=3)[CH:16]=[CH:15][C:14]=2[F:32])([CH3:12])[N:3]=1.[ClH:33]>CO.O1CCOCC1.[Pd]>[ClH:33].[NH:24]1[C:20]([NH:19][C:17]2[CH:16]=[CH:15][C:14]([F:32])=[C:13]([C@@:4]3([CH3:12])[N:3]=[C:2]([NH2:1])[N:7]([CH3:8])[C:6](=[O:9])[C:5]3([CH3:10])[CH3:11])[CH:18]=2)=[CH:21][CH:22]=[N:23]1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 57497035HCID 57497035, compound

Product 1

HCID 57497103HCID 57497103, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of (S)-2-amino-6-(5-(1-benzyl-1H-pyrazol-5-ylamino)-2-fluorophenyl)-3,5,5,6-tetramethyl-5,6-dihydropyrimidin-4(3H)-one (example 107, 0.02 mmole) in methanol (1 ml) was added a solution of aqueous 4M HCl in 1,4-dioxane (0.25 ml) and Pd/C (10%, 3 mg) under argon. The reaction mixture was hydrogenated at 1 atm H2 for 2 h, filtered over Decalite and the residue was washed with methanol. The filtrate was concentrated in vacuo and the residue purified by flash chromatography on NH2-silica using a gradient of dichloromethane/methanol to yield the title compound as a colorless waxy solid. MS (ESI): m/z=345.2 [M+H]+.

Workup

  1. filtrationfiltered over Decalite
  2. washthe residue was washed with methanol
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe residue purified by flash chromatography on NH2-silica using a gradient of dichloromethane/methanol

Sources & evidence

ORD record
ord-f63485deaba446969094def1f2ec7adc
Source dataset
uspto-grants-2014_08
Patent number
US08815881B2

Reaction notes

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