4-Aminobenzamide → 4-((4-(Benzyloxy)-5-iodopyrimidin-2-yl)amino)benzamide

HRID 2284762Notes

Reaction equation

HRID 2284762 reaction equation
[CH2:1]([O:8][C:9]1[C:14]([I:15])=[CH:13][N:12]=[C:11](Cl)[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:17][C:18]1[CH:26]=[CH:25][C:21]([C:22]([NH2:24])=[O:23])=[CH:20][CH:19]=1.[C@]12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O.C(=O)([O-])O.[Na+]>CN1CCCC1=O>[CH2:1]([O:8][C:9]1[C:14]([I:15])=[CH:13][N:12]=[C:11]([NH:17][C:18]2[CH:26]=[CH:25][C:21]([C:22]([NH2:24])=[O:23])=[CH:20][CH:19]=2)[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 760794-AminobenzamideHCID 218580(1S)-(+)-Camphor-10-sulphonic acidHCID 516892Sodium BicarbonateHCID 580535522-Chloro-5-iodo-4-(phenylmethoxy)pyrimidine

Product 1

HCID 900522984-((4-(Benzyloxy)-5-iodopyrimidin-2-yl)amino)benzamideYield 117.3%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 4-(benzyloxy)-2-chloro-5-iodopyrimidine (J1, 2.02 g) and 4-aminobenzamide (3.97 g) in N-methylpyrrolidone (20 mL), (1S)-(+)-10-camphorsulfonic acid (6.76 g) was added at room temperature, and the mixture was stirred at 60° C. for 9 hours. The reaction mixture was cooled on ice, and then poured into saturated aqueous sodium hydrogencarbonate. The solid matter was taken by filtration, washed with a mixed solvent of ethyl acetate and methanol, and then dried under reduced pressure to obtain 4-((4-(benzyloxy)-5-iodopyrimidin-2-yl)amino)benzamide (J10, 3.05 g) as white solid.

Workup

  1. temperatureThe reaction mixture was cooled on ice
  2. filtrationThe solid matter was taken by filtration
  3. washwashed with a mixed solvent of ethyl acetate and methanol
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-3dd42f03fd394857bdb81181405f21dd
Source dataset
uspto-grants-2015_09
Patent number
US09145415B2

Reaction notes

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