cis-(1-(4-Amino-5-nitropyrimidin-2-yl)-4-methylpiperidin-3-yl)(pyrrolidin-1-yl)methanone → cis-(1-(4,5-Diaminopyrimidin-2-yl)-4-methylpiperidin-3-yl)(pyrrolidin-1-yl)methanone

HRID 931307Notes

Reaction equation

HRID 931307 reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][N:5]=[C:4]([N:11]2[CH2:16][CH2:15][C@H:14]([CH3:17])[C@H:13]([C:18]([N:20]3[CH2:24][CH2:23][CH2:22][CH2:21]3)=[O:19])[CH2:12]2)[N:3]=1.[H][H]>C(O)C.[Pd]>[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][N:5]=[C:4]([N:11]2[CH2:16][CH2:15][C@H:14]([CH3:17])[C@H:13]([C:18]([N:20]3[CH2:24][CH2:23][CH2:22][CH2:21]3)=[O:19])[CH2:12]2)[N:3]=1

Participants

5

Reactant 2

HCID 89853969cis-(1-(4-Amino-5-nitropyrimidin-2-yl)-4-methylpiperidin-3-yl)(pyrrolidin-1-yl)methanoneHCID 178418361HCID 178418361, compound

Product 1

HCID 89853749cis-(1-(4,5-Diaminopyrimidin-2-yl)-4-methylpiperidin-3-yl)(pyrrolidin-1-yl)methanone

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

A suspension of 10% palladium-on-carbon (350 mg) in ethanol was added to a solution of cis-(1-(4-amino-5-nitropyrimidin-2-yl)-4-methylpiperidin-3-yl)(pyrrolidin-1-yl)methanone (600 mg, 1.79 mmol) in ethanol (20 mL) at room temperature under nitrogen. The mixture was hydrogenated using a balloon filled with hydrogen gas at room temperature for 2 h. The suspension was filtered through a pad of Celite under a nitrogen atmosphere and the filtrate was used for the next without further purification.

Workup

  1. filtrationThe suspension was filtered through a pad of Celite under a nitrogen atmosphere
  2. customnext without further purification

Sources & evidence

ORD record
ord-8e878c76ca5740a790791649467118b4
Source dataset
uspto-grants-2016_03
Patent number
US09296745B2

Reaction notes

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