Ethylamine → 4-(4-Ethylaminopyrimidin-6-yloxy)aniline

HRID 1993524Notes

Reaction equation

HRID 1993524 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([O:8][C:9]2[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=2)[CH:3]=1.[CH2:16]([NH2:18])[CH3:17]>C(O)C.O.CCOC(C)=O>[CH2:16]([NH:18][C:2]1[CH:3]=[C:4]([O:8][C:9]2[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=2)[N:5]=[CH:6][N:7]=1)[CH3:17]

Participants

6

Reactant 2

HCID 6341EthylamineHCID 226137114-((6-Chloropyrimidin-4-yl)oxy)aniline

Product 1

HCID 586593854-(4-Ethylaminopyrimidin-6-yloxy)aniline

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 4-(6-chloro-pyrimidin-4-yl-oxy)-aniline (Stage 21.1; 5.0 g, 22.6 mmol) in ethylamine dissolved in ethanol (≈35%; 5 ml) under Nratmosphere is stirred for 16 h at rt. Then the resulting brown solution is diluted with water and AcOEt, the aqueous layer separated off and extracted twice with AcOEt. The organic phases are washed with 3 portions of water and brine, dried (Na2SO4) and concentrated. Re-crystallisaton from boiling AcOEt gives the title compound: m.p.: 143-145° C.; 1H-NMR (CDCl3): 8.24 (s, 1H), 7.24 (s, HN), 6.91 (d, 2H), 6.69 (d, 2H), 5.63 (s, 1H), 4.97 (s, H2N), 3.25 (m, 2H), 1.25 (t, 3H). More product can be isolated from the filtrate of the re-crystallization by column chromatography (SiO2; AcOEt→AcOEt/EtOH 19:1).

Workup

  1. customthe aqueous layer separated off
  2. extractionextracted twice with AcOEt
  3. washThe organic phases are washed with 3 portions of water and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d38d5e655f464752bba3acfcd06a7c47
Source dataset
uspto-grants-2010_01
Patent number
US07652022B2

Reaction notes

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