Dimethylformamide → HCID 18921777, compound

HRID 1289571Notes

Reaction equation

HRID 1289571 reaction equation
[CH3:1][C:2]1[CH:8]=[C:7]([F:9])[CH:6]=[CH:5][C:3]=1[NH2:4].[CH3:10][C:11]1[N:16]=[C:15]([N:17]2[CH2:26][CH2:25][C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]2[CH3:27])[N:14]=[C:13]([Cl:28])[CH:12]=1.CN(C)C=O>ClCCl>[ClH:28].[CH3:10][C:11]1[N:16]=[C:15]([N:17]2[CH2:26][CH2:25][C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]2[CH3:27])[N:14]=[C:13]([NH:4][C:3]2[CH:5]=[CH:6][C:7]([F:9])=[CH:8][C:2]=2[CH3:1])[CH:12]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 679824-Fluoro-2-methylanilineHCID 18921675HCID 18921675, compound

Product 1

HCID 18921777HCID 18921777, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Methyl-4-fluoroaniline(1.1 ml, 10.2 mmol) was added to a mixture solution of 6-methyl-2-(1-methyl-1,2,3,4-tetrahydroisoquinolin-2-yl)-4-chloropyrimidine(1.5 g, 5.5 mmol) and dimethylformamide(10 ml). The reaction solution was stirred for 3 hours and cooled to room temperature. The reaction mixture was diluted with dichloromethane and washed with water. Dichloromethane layer was separated, basified with aqueous sodium hydroxide solution, washed with water, and dried and concentrated in vacuo. The resulting residue was purified with silica gel column chromatography to give a free base form of titled compound as an oily form. The free base form of titled compound was dissolved in ethyl ether, then hydrochloric acid was added thereto. The resulting solid was filtered, dried under reduced pressure to give 0.9 g of titled compound.

Workup

  1. washwashed with water
  2. customDichloromethane layer was separated
  3. washwashed with water
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified with silica gel column chromatography

Sources & evidence

ORD record
ord-6bd0369cfd3148e49c4968f498da12ac
Source dataset
uspto-grants-1998_05
Patent number
US05750531

Reaction notes

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