2-(4,6-Dimethoxy-5-nitropyrimidin-2-yl)-1,2,3,4-tetrahydroisoquinoline → 2-(3,4-dihydroisoquinolin-2(1H)-yl)-4,6-dimethoxypyrimidin-5-amine

HRID 383709Notes

Reaction equation

HRID 383709 reaction equation
[CH3:1][O:2][C:3]1[C:8]([N+:9]([O-])=O)=[C:7]([O:12][CH3:13])[N:6]=[C:5]([N:14]2[CH2:23][CH2:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:15]2)[N:4]=1.[H][H]>[Ni]>[CH2:15]1[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:22][CH2:23][N:14]1[C:5]1[N:6]=[C:7]([O:12][CH3:13])[C:8]([NH2:9])=[C:3]([O:2][CH3:1])[N:4]=1

Participants

4

Reactant 2

HCID 598687192-(4,6-Dimethoxy-5-nitropyrimidin-2-yl)-1,2,3,4-tetrahydroisoquinolineHCID 178418361HCID 178418361, compound

Product 1

HCID 598688212-(3,4-dihydroisoquinolin-2(1H)-yl)-4,6-dimethoxypyrimidin-5-amine

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

A suspension of Raney®-Nickel in a methanolic solution of 4b (0.57 g in 50 ml, 1.8 mmol) was shaken under 50 psi of hydrogen atmosphere for 12 hours. The mixture was filtered and the filtrate was concentrated and used for the next step without further purification (0.51 g, 1.78 mmol, 99%).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. customused for the next step without further purification (0.51 g, 1.78 mmol, 99%)

Sources & evidence

ORD record
ord-6aa452ca32e84db08b114e465449b063
Source dataset
uspto-grants-2013_02
Patent number
US08367684B2

Reaction notes

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