(R)-4-chloro-6-((1-methylpiperidin-3-yl)oxy)pyrimidin-5-amine → (R)-4((1-methylpiperidin-3-yl)oxy)pyrimidin-5-amine

HRID 1850682Notes

Reaction equation

HRID 1850682 reaction equation
Cl[C:2]1[C:7]([NH2:8])=[C:6]([O:9][C@@H:10]2[CH2:15][CH2:14][CH2:13][N:12]([CH3:16])[CH2:11]2)[N:5]=[CH:4][N:3]=1>CO.[Pd]>[CH3:16][N:12]1[CH2:13][CH2:14][CH2:15][C@@H:10]([O:9][C:6]2[C:7]([NH2:8])=[CH:2][N:3]=[CH:4][N:5]=2)[CH2:11]1

Participants

4

Reactant 1

HCID 90411331(R)-4-chloro-6-((1-methylpiperidin-3-yl)oxy)pyrimidin-5-amine

Product 1

HCID 90411653(R)-4((1-methylpiperidin-3-yl)oxy)pyrimidin-5-amineYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(R)-4-chloro-6-((1-methylpiperidin-3-yl)oxy)pyrimidin-5-amine was dissolved in MeOH (15.0 mL) and Pd/C 10% (324.5 mg, 0.3049 mmol) was added and the reaction mixture stirred under a hydrogen atmosphere for 2 h. The reaction vessel was evacuated and flushed with nitrogen (3×), filtered through a celite pad washing with methanol followed by ethyl acetate. The combined filtrates were concentrated in vacuo to leave the title product 7a as a colourless oil (631 mg, 99%).

Workup

  1. customThe reaction vessel was evacuated
  2. customflushed with nitrogen (3×)
  3. filtrationfiltered through a celite pad
  4. washwashing with methanol
  5. concentrationThe combined filtrates were concentrated in vacuo

Sources & evidence

ORD record
ord-5811122b801a46ee9ccb51820b1fdb65
Source dataset
uspto-grants-2015_02
Patent number
US08957078B2

Reaction notes

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