Dimethylformamide → HCID 178429391, compound

HRID 1289569Notes

Reaction equation

HRID 1289569 reaction equation
[CH3:1][C:2]1[N:7]=[C:6](Cl)[N:5]=[C:4]([OH:9])[CH:3]=1.[CH3:10][CH:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][CH2:13][NH:12]1.CN(C)C=O>ClCCl.CO>[CH3:1][C:2]1[N:7]=[C:6]([N:12]2[CH2:13][CH2:14][C:15]3[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:11]2[CH3:10])[N:5]=[C:4]([OH:9])[CH:3]=1

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 922141-Methyl-1,2,3,4-tetrahydroisoquinolineHCID 178429342HCID 178429342, compound

Product 1

HCID 178429391HCID 178429391, compoundYield 74.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture solution of 6-methyl-2-chloro-4-hydroxypyrimidine(6 g, 37.5 mmol) prepared in the above Step 1, 1-methyl-1,2,3,4-tetrahydroisoquinoline(11.6 g, 78.8 mmol) and N,N-dimethylformamide(30 ml) was stirred at 120 for 2 hours and cooled to give a solid. The resulting solid was dissolved in a mixture solution of dichloromethane and methanol and the undissolved materials were filtered off. The filtrate residue was washed many times with water, dried over anhydrous sodium sulfate, concentrated under reduced pressure to give 7.1 g of titled compound. (Yield: 74.1%)

Workup

  1. temperaturecooled
  2. customto give a solid
  3. filtrationthe undissolved materials were filtered off
  4. washThe filtrate residue was washed many times with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3c59bf8f11434dfe913dff2d5318f18e
Source dataset
uspto-grants-1998_05
Patent number
US05750531

Reaction notes

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