3-Fluoroaniline → HCID 90051756, compound

HRID 2284712Notes

Reaction equation

HRID 2284712 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH2:10][CH3:11])[C:5]([I:12])=[CH:4][N:3]=1.[F:13][C:14]1[CH:15]=[C:16]([CH:18]=[CH:19][CH:20]=1)[NH2:17].[C@]12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O.C(=O)([O-])O.[Na+]>CN1CCCC1=O>[F:13][C:14]1[CH:15]=[C:16]([NH:17][C:2]2[N:7]=[C:6]([NH:8][CH2:9][CH2:10][CH3:11])[C:5]([I:12])=[CH:4][N:3]=2)[CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 97423-FluoroanilineHCID 218580(1S)-(+)-Camphor-10-sulphonic acidHCID 516892Sodium BicarbonateHCID 900517702-chloro-5-iodo-N-propylpyrimidin-4-amine

Product 1

HCID 90051756HCID 90051756, compoundYield 91.9%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of 2-chloro-5-iodo-N-propylpyrimidin-4-amine (F1, 596 mg) and 3-fluoroaniline (1.11 g) in N-methylpyrrolidone (10 mL), (1S)-(+)-10-camphorsulfonic acid (2.32 g) was added at room temperature, and the mixture was stirred at 40 to 50° C. for 6 hours. The reaction mixture was cooled to room temperature, and then saturated aqueous sodium hydrogencarbonate was added to the reaction mixture. The solid matter was taken by filtration, washed with water, and then dried under reduced pressure to obtain N2-(3-fluorophenyl)-5-iodo-N4-propylpyrimidine-2,4-diamine (F2, 685 mg) as white solid.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationThe solid matter was taken by filtration
  3. washwashed with water
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-220fb9a7ce50424dab3cadb6aa95c8cd
Source dataset
uspto-grants-2015_09
Patent number
US09145415B2

Reaction notes

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