HCID 56967605, compound → HCID 67502555, compound

HRID 1187766Notes

Reaction equation

HRID 1187766 reaction equation
[NH2:1][C:2]1[O:3][CH2:4][C@H:5]([CH2:7][CH2:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]3[CH:21]=[C:20]([Cl:22])[N:19]=[CH:18][N:17]=3)=[CH:11][CH:10]=2)[N:6]=1>CO>[ClH:22].[N:19]1[CH:20]=[CH:21][C:16]([NH:15][C:12]2[CH:11]=[CH:10][C:9]([CH2:8][CH2:7][C@H:5]3[CH2:4][O:3][C:2]([NH2:1])=[N:6]3)=[CH:14][CH:13]=2)=[N:17][CH:18]=1

Participants

3

Reactant 1

HCID 56967605HCID 56967605, compound

Product 1

HCID 67502555HCID 67502555, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

{4-[2-((S)-2-Amino-4,5-dihydro-oxazol-4-yl)-ethyl]-phenyl}-(6-chloro-pyrimidin-4-yl)-amine (16 mg, Example 32) was dissolved in methanol to give a colourless solution. The mixture was degassed by bubbling through argon for several minutes. 10% Palladium on charcoal (11 mg) was added and the reaction mixture was stirred under a hydrogen-filled balloon at room temperature for 2 hours. The reaction mixture was filtered through celite and the filtrate was concentrated in vacuo to afford (S)-4-(4-(pyrimidin-4-ylamino)phenethyl)-4,5-dihydrooxazol-2-amine hydrochloride (14 mg, 87%) as a white solid. MS (ISP): 284.2 ([M+H]+).

Workup

  1. customto give a colourless solution
  2. customThe mixture was degassed
  3. customby bubbling through argon for several minutes
  4. addition10% Palladium on charcoal (11 mg) was added
  5. additionfilled balloon at room temperature for 2 hours
  6. filtrationThe reaction mixture was filtered through celite
  7. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-f562b76cbcd04cd9bbb8b4630186a442
Source dataset
uspto-grants-2014_03
Patent number
US08673950B2

Reaction notes

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