Water → 4-Amino-6-(4-nitrophenoxy)pyrimidine

HRID 853509Notes

Reaction equation

HRID 853509 reaction equation
Cl[C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=2)[N:5]=[CH:4][N:3]=1.[NH3:18].C(O)C.C(OCC)(=O)C.O>CCCCCC>[N+:15]([C:12]1[CH:13]=[CH:14][C:9]([O:8][C:6]2[N:5]=[CH:4][N:3]=[C:2]([NH2:18])[CH:7]=2)=[CH:10][CH:11]=1)([O-:17])=[O:16]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl Acetate2×HCID 143638504-Chloro-6-(4-nitrophenoxy)pyrimidineHCID 22020343Ethanol, reaction products with ammonia, distn. residues

Product 1

HCID 229369424-Amino-6-(4-nitrophenoxy)pyrimidineYield 33%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

4-Chloro-6-(4-nitrophenoxy)pyrimidine (1.04 g, 4.00 mmol) was heated and stirred in an ammonia-ethanol solution (14%, 10 ml) at 110° C. for 15 minutes using an autoclave. The reaction solution was distributed between ethyl acetate and water, the organic layer was washed with 1N aqueous sodium hydroxide, water and saturated brine and dried over anhydrous magnesium sulfate, the drying agent was filtered off and the filtrate was distilled off under reduced pressure. The obtained crude product was subjected to silica gel column chromatography (eluent—ethyl acetate:hexane=1:1), and the fraction containing the target substance was concentrated to obtain the title compound (306 mg, 1.32 mmol, 33%) as colorless crystals.

Workup

  1. washthe organic layer was washed with 1N aqueous sodium hydroxide, water and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationthe drying agent was filtered off
  4. distillationthe filtrate was distilled off under reduced pressure
  5. customThe obtained crude product
  6. additionthe fraction containing the target substance
  7. concentrationwas concentrated

Sources & evidence

ORD record
ord-5bd86fa7d09546ba8d296b50dfc96038
Source dataset
uspto-grants-2007_08
Patent number
US07253286B2

Reaction notes

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