Dimethylformamide → HCID 18921678, compound

HRID 1289496Notes

Reaction equation

HRID 1289496 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.[CH3:9][CH:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:13][CH2:12][NH:11]1.C(N(CC)CC)C.CN(C)C=O>ClCCl>[CH3:9][CH:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:13][CH2:12][N:11]1[C:6]1[CH:5]=[CH:4][N:3]=[C:2]([Cl:1])[N:7]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 775312,4-DichloropyrimidineHCID 922141-Methyl-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 18921678HCID 18921678, compoundYield 28.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture solution of 2,4-dichloropyrimidine(3.0 g, 20 mmol), 1-methyl-1,2,3,4-tetrahydroisoquinoline(3.3 g, 22 mmol), triethylamine(3.4 ml, 24.4 mmol) and N,N-dimethyl formamide(20 ml) was stirred for 5 hours, diluted with dichloromethane, washed with water several times. The dichloromethane layer was separated, dried over anhydrous sodium sulfate and then concentrated under a reduced pressure. The resulting residue was crystallized by silica gel column chromatography to give 1.5 g of the titled compound. (Yield: 28.9%)

Workup

  1. washwashed with water several times
  2. customThe dichloromethane layer was separated
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under a reduced pressure
  5. customThe resulting residue was crystallized by silica gel column chromatography

Sources & evidence

ORD record
ord-8d41226747784e2daee9ddc92ffd434d
Source dataset
uspto-grants-1998_05
Patent number
US05750531

Reaction notes

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