Dimethylformamide → HCID 18921773, compound

HRID 1289497Notes

Reaction equation

HRID 1289497 reaction equation
[CH3:1][C:2]1[CH:8]=[C:7]([F:9])[CH:6]=[CH:5][C:3]=1[NH2:4].[CH3:10][CH:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][CH2:13][N:12]1[C:21]1[CH:26]=[CH:25][N:24]=[C:23]([Cl:27])[N:22]=1.CN(C)C=O>ClCCl>[ClH:27].[CH3:1][C:2]1[CH:8]=[C:7]([F:9])[CH:6]=[CH:5][C:3]=1[NH:4][C:23]1[N:22]=[C:21]([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])[CH:26]=[CH:25][N:24]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 679824-Fluoro-2-methylanilineHCID 18921678HCID 18921678, compound

Product 1

HCID 18921773HCID 18921773, 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 4-(1-methyl-1,2,3,4-tetrahydroisoquinolin-2-yl)-2-chloropyrimidine(1.5 g, 5.8 mmol) and dimethylformamide(10 ml). The reaction mixture was stirred for 3 hours at 110°-120° C., cooled to a room temperature, diluted with dichloromethane, and then washed with water. The dichloromethane layer was separated, basified with aqueous sodium hydroxide, washed with water, dried and concentrated. The resulting residue was crystallized by silica gel column chromatography to give free base form of the titled compound. To a mixture solution of the free base form of the titled compound and ethyl ether was added aqueous hydrochloric acid and the resulting titled compound was filtered and dried in vacuo. Recrystallization from ethanol afforded 1.2 g of the titled compound as a white crystalline solid.

Workup

  1. washwashed with water
  2. customThe dichloromethane layer was separated
  3. washwashed with water
  4. customdried
  5. concentrationconcentrated
  6. customThe resulting residue was crystallized by silica gel column chromatography

Sources & evidence

ORD record
ord-b0c5ef09f6b44cbdab4d89004259ada9
Source dataset
uspto-grants-1998_05
Patent number
US05750531

Reaction notes

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