HCID 66916106, compound → HCID 59205159, compound

HRID 2061437Notes

Reaction equation

HRID 2061437 reaction equation
[CH2:1]([O:4][C:5]1[C:10]([S:11]([NH2:14])(=[O:13])=[O:12])=[C:9]([NH2:15])[CH:8]=[CH:7][CH:6]=1)[CH:2]=[CH2:3].Cl[C:17]1[CH:22]=[CH:21][N:20]=[C:19]([NH:23][C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[C:26]([O:32][CH3:33])[CH:25]=2)[N:18]=1>CC(O)C.Cl>[CH2:1]([O:4][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]([NH:15][C:21]2[CH:22]=[CH:17][N:18]=[C:19]([NH:23][C:24]3[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[C:26]([O:32][CH3:33])[CH:25]=3)[N:20]=2)[C:10]=1[S:11]([NH2:14])(=[O:13])=[O:12])[CH:2]=[CH2:3]

Participants

5

Reactant 2

HCID 66916106HCID 66916106, compoundHCID 86608852HCID 86608852, compound

Product 1

HCID 59205159HCID 59205159, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 3776IsopropanolSolvent

Procedure

A solution of 6-Allyloxy-2-aminophenyl-sulfonamide (38 mg, 0.166 mmol) and 4-chloro-2-(3,4-dimethoxy-phenylamino)pyrimidine (44.2 mg, 0.166 mmol) in 2-propanol (5 ml) and 1N HCl (333 μl) is refluxed for 105 min. The reaction mixture is partitioned between ammonia (pH 10-11) and EtOAc. The organic layer is dried (Na2SO4) and concentrated. Precipitation with ether/hexanes gives the desired 2-Allyloxy-6-[2-(3,4-dimethoxy-phenylamino)-pyrimidin-4-ylamino]-benzenesulfonamide.

Workup

  1. customThe reaction mixture is partitioned between ammonia (pH 10-11) and EtOAc
  2. dry with materialThe organic layer is dried (Na2SO4)
  3. concentrationconcentrated
  4. customPrecipitation with ether/hexanes

Sources & evidence

ORD record
ord-160f2f43a16444a68410eb76b98df035
Source dataset
uspto-grants-2012_10
Patent number
US08283356B2

Reaction notes

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