4-Amino-6-chloropyrimidine → HCID 59864576, Verbindung

HRID 409654

Reaktionsgleichung

Reaktionsgleichung von HRID 409654
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH2:8])[CH:3]=1.[N:9]1([CH2:15][CH2:16][O:17][C:18]2[CH:23]=[CH:22][C:21]([NH2:24])=[CH:20][CH:19]=2)[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1>O.C(O)(=O)C>[N:9]1([CH2:15][CH2:16][O:17][C:18]2[CH:23]=[CH:22][C:21]([NH:24][C:2]3[CH:3]=[C:4]([NH2:8])[N:5]=[CH:6][N:7]=3)=[CH:20][CH:19]=2)[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1

Komponenten

5

Edukt 2

HCID 2380124-Amino-6-chloropyrimidineHCID 64847114-(2-Morpholinoethoxy)aniline

Produkt 1

HCID 59864576HCID 59864576, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 6-chloro-pyrimidin-4-ylamine (194 mg, 1.5 mmol, 1.3 equiv), 4-(2-morpholin-4-yl-ethoxy)-phenylamine (256 mg, 1.15 mmol) in H2O (1 mL) and glacial acetic acid (5 mL) is stirred for 16 h at 100° C. After solvent evaporation, the residue is taken up in DCM and diluted with a saturated aqueous solution of NaHCO3. The aqueous layer is separated and extracted with DCM. The organic phase is washed with brine, dried (Na2SO4), filtered and concentrated. The residue is triturated in EtOAc to provide the title compound as a grey solid: ESI-MS: 316.2 [MH]+; tR=1.00 min (purity: 95%, system 1); TLC: Rf=0.22 (DCM/MeOH+1% NH3aq, 93:7).

Aufarbeitung

  1. customAfter solvent evaporation
  2. additiondiluted with a saturated aqueous solution of NaHCO3
  3. customThe aqueous layer is separated
  4. extractionextracted with DCM
  5. washThe organic phase is washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue is triturated in EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-71a74807b003482ca13a3ede60901537
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08759517B2

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