Methanone, [(3R)-1-(4-amino-5-nitro-2-pyrimidinyl)-3-piperidinyl]-1-pyrrolidinyl- → (R)-(1-(4,5-diaminopyrimidin-2-yl)piperidin-3-yl)(pyrrolidin-1-yl)methanone

HRID 931061Notes

Reaction equation

HRID 931061 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][CH2:14][C@@H:13]([C:17]([N:19]3[CH2:23][CH2:22][CH2:21][CH2:20]3)=[O:18])[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][CH2:14][C@@H:13]([C:17]([N:19]3[CH2:23][CH2:22][CH2:21][CH2:20]3)=[O:18])[CH2:12]2)[N:3]=1

Participants

5

Reactant 2

HCID 89854015Methanone, [(3R)-1-(4-amino-5-nitro-2-pyrimidinyl)-3-piperidinyl]-1-pyrrolidinyl-HCID 178418361HCID 178418361, compound

Product 1

HCID 89853288(R)-(1-(4,5-diaminopyrimidin-2-yl)piperidin-3-yl)(pyrrolidin-1-yl)methanone

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

To a stirred solution of (R)-(1-(4-amino-5-nitropyrimidin-2-yl)piperidin-3-yl)(pyrrolidin-1-yl)methanone (300 mg, 0.937 mmol) in ethanol (15 mL) was added under a nitrogen atmosphere a suspension of 10% palladium-on-carbon (300 mg) in ethanol. The reaction mixture was hydrogenated using a balloon filled with hydrogen gas for 2 h at room temperature. The suspension was filtered through Celite and the filtrate was used without further purification.

Workup

  1. filtrationThe suspension was filtered through Celite
  2. customthe filtrate was used without further purification

Sources & evidence

ORD record
ord-86ea8aea5c8f42c79b3f3e377af94474
Source dataset
uspto-grants-2016_03
Patent number
US09296745B2

Reaction notes

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