Hydrochloric Acid → HCID 57708307, compound

HRID 929844Notes

Reaction equation

HRID 929844 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([O:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:10]=2)[CH:3]=1.[NH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([NH2:29])[CH:24]=1.Cl>C(O)CCC>[NH2:22][C:23]1[CH:24]=[C:25]([NH:29][C:2]2[CH:3]=[C:4]([NH:8][C:9]3[CH:14]=[CH:13][CH:12]=[C:11]([O:15][C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[CH:10]=3)[N:5]=[CH:6][N:7]=2)[CH:26]=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7935M-PhenylenediamineHCID 57708302HCID 57708302, compound

Product 1

HCID 57708307HCID 57708307, compoundYield 33.8%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A solution of 6-chloro-N-(3-phenoxyphenyl)pyrimidine-4-amine (0.25 g, 0.8 mmol), 1,3-diaminobenzene (0.36 g, 3.3 mmol), n-butanol (10 mL) and conc. HCl (61 mg, 1.6 mmol) was subjected to microwave irradiation (160° C., 15 min). The reaction mixture was cooled, was concentrated under reduced pressure and the residue was taken in EtOAc (10 mL). The EtOAc solution was washed with water (5 mL) and brine (5 mL), and was dried over Na2SO4. Concentration under reduced pressure gave a residue that was purified by column chromatography (SiO2, 60-120, hexane/ethyl acetate, 6/4) to give N4-(3-aminophenyl)-N6-(3-phenoxyphenyl)pyrimidine-4,6-diamine (0.1 g, 32%) as a brown solid.

Workup

  1. temperatureThe reaction mixture was cooled
  2. concentrationwas concentrated under reduced pressure
  3. washThe EtOAc solution was washed with water (5 mL) and brine (5 mL)
  4. dry with materialwas dried over Na2SO4
  5. concentrationConcentration under reduced pressure
  6. customgave a residue that
  7. customwas purified by column chromatography (SiO2, 60-120, hexane/ethyl acetate, 6/4)

Sources & evidence

ORD record
ord-75abc0bdd1264ce991f13a7c402fbee2
Source dataset
uspto-grants-2016_03
Patent number
US09296704B2

Reaction notes

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