1,2,3,4-Tetrahydroisoquinoline → HCID 11784505, compound

HRID 378912Notes

Reaction equation

HRID 378912 reaction equation
[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[N:10]=[C:9]([Cl:11])[N:8]=[C:7](Cl)[C:6]=2[N:13]=1.[CH2:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:18][CH2:17][NH:16]1>C1COCC1>[Cl:1][C:2]1[N:3]=[C:4]([N:16]2[CH2:17][CH2:18][C:19]3[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:15]2)[C:5]2[N:10]=[C:9]([Cl:11])[N:8]=[C:7]([N:16]3[CH2:17][CH2:18][C:19]4[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH2:15]3)[C:6]=2[N:13]=1

Participants

4

Reactant 2

HCID 70461,2,3,4-TetrahydroisoquinolineHCID 97007Tetrachloropyrimido(5,4-d)pyrimidine

Product 1

HCID 11784505HCID 11784505, compoundYield 7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
25 °C

Procedure

To a solution of 2,4,6,8-tetrachloropyrimidopyrimidine (0.54 g, 8.0 mmol) in THF (50 ml) was added a solution of 1,2,3,4-tetrahydroisoquinoline (1.0 ml) in THF (15 ml) dropwise over 10 minutes. The mixture was stirred for 12 hours at 25° C., the resultant solid was removed by filtration. The filtrate was evaporated under reduced pressure to afford a brown solid. Chromatography on silica gel, employing petrol:EtOAc (8:2) as eluent, afforded the title compound as a pale brown powder (0.27 g, 7%).

Workup

  1. customthe resultant solid was removed by filtration
  2. customThe filtrate was evaporated under reduced pressure
  3. customto afford a brown solid

Sources & evidence

ORD record
ord-875d1a96dd4a4b11a4d556f54e97ce04
Source dataset
uspto-grants-2001_10
Patent number
US06297250B1

Reaction notes

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