(R)-(4-(4-amino-5-nitropyrimidin-2-yl)morpholin-2-yl)(pyrrolidin-1-yl)methanone → (R)-(4-(4,5-Diaminopyrimidin-2-yl)morpholin-2-yl)(pyrrolidin-1-yl)methanone

HRID 931319Notes

Reaction equation

HRID 931319 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][O: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][O: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 89854246(R)-(4-(4-amino-5-nitropyrimidin-2-yl)morpholin-2-yl)(pyrrolidin-1-yl)methanoneHCID 178418361HCID 178418361, compound

Product 1

HCID 89853939(R)-(4-(4,5-Diaminopyrimidin-2-yl)morpholin-2-yl)(pyrrolidin-1-yl)methanone

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of (R)-(4-(4-amino-5-nitropyrimidin-2-yl)morpholin-2-yl)(pyrrolidin-1-yl)methanone (0.15 g, 0.46 mmol) in ethanol (15 mL) was added 10% palladium-on-carbon (300 mg). The mixture was hydrogenated using a balloon filled with hydrogen gas at room temperature for 3 h. The mixture was filtered through a pad of Celite and the filtrate was used for the next step without further purification.

Workup

  1. filtrationThe mixture was filtered through a pad of Celite
  2. customthe filtrate was used for the next step without further purification

Sources & evidence

ORD record
ord-b8536b181f1e4f56bcf65978a6f8285d
Source dataset
uspto-grants-2016_03
Patent number
US09296745B2

Reaction notes

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