1,2,3,4-Tetrahydroisoquinoline → 2-(4,6-Dimethoxy-5-nitropyrimidin-2-yl)-1,2,3,4-tetrahydroisoquinoline

HRID 383708Notes

Reaction equation

HRID 383708 reaction equation
[N:1]12[CH2:11][CH2:10][CH2:9]N=[C:7]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2.Cl[C:13]1[N:18]=[C:17]([O:19][CH3:20])[C:16]([N+:21]([O-:23])=[O:22])=[C:15]([O:24][CH3:25])[N:14]=1.C1C2C(=CC=CC=2)CCN1>CN(C=O)C>[CH3:25][O:24][C:15]1[C:16]([N+:21]([O-:23])=[O:22])=[C:17]([O:19][CH3:20])[N:18]=[C:13]([N:1]2[CH2:11][CH2:10][C:9]3[C:6](=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH2:7]2)[N:14]=1

Participants

5

Reactant 3

HCID 70461,2,3,4-TetrahydroisoquinolineHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 109985372-Chloro-4,6-dimethoxy-5-nitropyrimidine

Product 1

HCID 598687192-(4,6-Dimethoxy-5-nitropyrimidin-2-yl)-1,2,3,4-tetrahydroisoquinolineYield 94%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1,8-diazabicyclo[5.4.0]undec-7-ene (0.304 g, 2 mmol) was added to a mixture of 4a (0.438 g, 2 mmol) and 1,2,3,4-tetrahydroisoquinoline (0.293 g, 2.2 mmol) in DMF (3 ml) at 0° C. over 5 minutes. The mixture was stirred for an additional 5 minutes at room temperature. The mixture was washed with brine, extracted with ethyl acetate and chromatographed to yield 4b (0.592 g, 1.87 mmol, 94%).

Workup

  1. washThe mixture was washed with brine
  2. extractionextracted with ethyl acetate
  3. customchromatographed

Sources & evidence

ORD record
ord-fb3107fc5d6e4a10aaabdfd210221a2e
Source dataset
uspto-grants-2013_02
Patent number
US08367684B2

Reaction notes

Loading…