(3,4-dihydro-1H-isochromen-1-ylmethyl)amine → (6-Chloro-2-methoxy-pyrimidin-4-yl)-isochroman-1-ylmethyl-amine

HRID 216255Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 216255
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([O:9][CH3:10])[N:3]=1.[CH:11]1([CH2:21][NH2:22])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][CH2:13][O:12]1.C([O-])(O)=O.[Na+]>CCO.O>[Cl:8][C:6]1[N:5]=[C:4]([O:9][CH3:10])[N:3]=[C:2]([NH:22][CH2:21][CH:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH2:14][CH2:13][O:12]2)[CH:7]=1

Komponenten

6

Edukt 3

HCID 209070(3,4-dihydro-1H-isochromen-1-ylmethyl)amineHCID 516892Sodium BicarbonateHCID 120521604,6-Dichloro-2-methoxypyrimidine

Produkt 1

HCID 86615712(6-Chloro-2-methoxy-pyrimidin-4-yl)-isochroman-1-ylmethyl-amineAusbeute 109,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 4,6-dichloro-2-methoxy-pyrimidine (0.45 g, 2.5 mmol), C-isochroman-1-yl-methylamine (0.53 g, 3.2 mmol), and NaHCO3 (0.63 g, 7.5 mmol) in EtOH (5 mL) is heated to reflux for 4 h. The mixture is diluted with water, concentrated in vacuo. The residue is partitioned between EtOAc and water, and extracted with EtOAc. The extracts are dried (Na2SO4), and concentrated to afford (6-chloro-2-methoxy-pyrimidin-4-yl)-isochroman-1-ylmethyl-amine (0.84 g). LCMS: RT=2.94 minutes; MS: 306 (M+H).

Aufarbeitung

  1. temperatureis heated
  2. temperatureto reflux for 4 h
  3. concentrationconcentrated in vacuo
  4. customThe residue is partitioned between EtOAc and water
  5. extractionextracted with EtOAc
  6. dry with materialThe extracts are dried (Na2SO4)
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-3cd611459e61428ebfba335b14970b4e
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08193183B2

Notizen zur Reaktion

Wird geladen…