N,N-Dimethylaniline → HCID 18921675, compound

HRID 1289570Notes

Reaction equation

HRID 1289570 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:17][CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]2[CH3:18])[N:5]=[C:4](O)[CH:3]=1.CN(C)C1C=CC=CC=1.C(=O)(O)[O-].[Na+].P(Cl)(Cl)([Cl:36])=O>>[CH3:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:17][CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]2[CH3:18])[N:5]=[C:4]([Cl:36])[CH:3]=1

Participants

5

Reactant 4

HCID 949N,N-DimethylanilineHCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 178429391HCID 178429391, compound

Product 1

HCID 18921675HCID 18921675, compoundYield 60%

Conditions

Temperature
90 °C

Procedure

A mixture solution of 6-methyl-2-(1-methyl-1,2,3,4-tetrahydroisoquinolin-2-yl)-4-hydroxypyrimidine(7.0 g, 27.4 mmol) prepared in the above Step 2, phosphorous oxychloride(30 ml) and N,N-dimethylaniline(2. 3 ml) was stirred at 90° C. for 2 hours and cooled. The reaction mixture was added to ice water and basified with sodium bicarbonate and then was extracted with ethyl ether. The ethyl ether layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give 4.5 g of titled compound.

Workup

  1. temperaturecooled
  2. extractionwas extracted with ethyl ether
  3. dry with materialThe ethyl ether layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-49d0e90feb754546980ee562b9d4af15
Source dataset
uspto-grants-1998_05
Patent number
US05750531

Reaction notes

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