Ethanol → HCID 20437718, compound

HRID 1979952Notes

Reaction equation

HRID 1979952 reaction equation
[OH-].[Na+].Cl.[CH3:4][O:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][C:15]=1[O:16][CH3:17])[CH2:12][NH:11][CH2:10][CH2:9]2.[Cl:18][C:19]1[CH:24]=[C:23](Cl)[N:22]=[CH:21][N:20]=1.C(O)C>O.C(O)(C)C>[Cl:18][C:19]1[CH:24]=[C:23]([N:11]2[CH2:10][CH2:9][C:8]3[C:13](=[CH:14][C:15]([O:16][CH3:17])=[C:6]([O:5][CH3:4])[CH:7]=3)[CH2:12]2)[N:22]=[CH:21][N:20]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 14798Sodium HydroxideHCID 709434,6-DichloropyrimidineHCID 64560356,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride

Product 1

HCID 20437718HCID 20437718, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

Sodium hydroxide solution (80 ml, IN) was added to a suspension of 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride in water (20 ml) followed by 4,6-dichloropyrimidine (5.95 g) and the mixture was heated on a steam bath for 5 hours. The solvent was evaporated in vacuo to give a brown oil which solidified on standing. Re-crystallization from aqueous ethanol followed by isopropanol gave 4-chloro-6-(6,7-dimethoxy-1,2,3,4-tetrahydroisoquinol-2-yl)pyrimidine (6.0 g). An analytical sample re-crystallized from isopropanol, m.p. 88°-89°.

Workup

  1. temperaturethe mixture was heated on a steam bath for 5 hours
  2. customThe solvent was evaporated in vacuo
  3. customto give a brown oil which

Sources & evidence

ORD record
ord-8b01ef03f4f14677917f5a8f2ec81880
Source dataset
uspto-grants-1984_11
Patent number
US04483859

Reaction notes

Loading…