Dimethylformamide → HCID 18921711, compound

HRID 1289534Notes

Reaction equation

HRID 1289534 reaction equation
[CH3:1][CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][NH:3]1.C(N(CC)CC)C.CN(C)C=O.[Cl:24][C:25]1[N:34]=[C:33](Cl)[C:32]2[CH2:31][CH2:30][CH2:29][CH2:28][C:27]=2[N:26]=1>C(OCC)(=O)C>[CH3:1][CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][N:3]1[C:33]1[C:32]2[CH2:31][CH2:30][CH2:29][CH2:28][C:27]=2[N:26]=[C:25]([Cl:24])[N:34]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 922141-Methyl-1,2,3,4-tetrahydroisoquinolineHCID 126028642,4-Dichloro-5,6,7,8-tetrahydroquinazoline

Product 1

HCID 18921711HCID 18921711, compoundYield 62.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture solution of 1-methyl-1,2,3,4-tetrahydroisoquinoline(2.6 g, 17.4 mmol), triethylamine(2.8 mL), N,N-dimethylformamide (20 ml) and 2,4-dichloro-5,6,7,8-tetrahydroquinazoline(3.2 g, 15.8 mmol) prepared in the above Step 2 were stirred at 80° C. for 3 hours and cooled. The reaction mixture was diluted with ethyl acetate and washed with water. The organic layer was separated, dried over anhydrous sodium sulfate, and concentrated. The residue was purified with silica gel column chromatography to give 3.1 g of the titled compound. (Yield: 62.5%)

Workup

  1. temperaturecooled
  2. washwashed with water
  3. customThe organic layer was separated
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified with silica gel column chromatography

Sources & evidence

ORD record
ord-4c5f0970699f4d0a9294a378b078ea4e
Source dataset
uspto-grants-1998_05
Patent number
US05750531

Reaction notes

Loading…