Potassium Phosphate, Tribasic → 6-(2-Chloro-pyrimidin-4-yloxy)-benzo[d]isoxazole-3-carboxylic acid ethyl ester

HRID 556350

Reaktionsgleichung

Reaktionsgleichung von HRID 556350
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.[CH2:9]([O:11][C:12]([C:14]1[C:18]2[CH:19]=[CH:20][C:21]([OH:23])=[CH:22][C:17]=2[O:16][N:15]=1)=[O:13])[CH3:10].[O-]P([O-])([O-])=O.[K+].[K+].[K+]>CN1C(=O)CCC1.C(Cl)Cl.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[CH2:9]([O:11][C:12]([C:14]1[C:18]2[CH:19]=[CH:20][C:21]([O:23][C:6]3[CH:5]=[CH:4][N:3]=[C:2]([Cl:1])[N:7]=3)=[CH:22][C:17]=2[O:16][N:15]=1)=[O:13])[CH3:10]

Komponenten

7

Edukt 3

HCID 62657Potassium Phosphate, TribasicHCID 775312,4-DichloropyrimidineHCID 136216618Ethyl 6-hydroxybenzo[d]isoxazole-3-carboxylate

Produkt 1

HCID 866266246-(2-Chloro-pyrimidin-4-yloxy)-benzo[d]isoxazole-3-carboxylic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 311Citric AcidLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Versuchsvorschrift

A suspension of 2.7 g (18.1 mMol) 2,4-dichloropyrimidine, 4.12 g (19.9 mMol) 6-hydroxy-benzo[d]isoxazole-3-carboxylic acid ethyl ester [preparation see: J. Am. Chem. Soc. 97 (1974), 7305] and 8.45 g (39.8 mMol) K3PO4 in 90 ml NMP is stirred for 22 h at rt. Then the mixture is diluted with 0.5 l CH2Cl2 and 0.9 l of a 5% citric acid solution. The organic phase is separated off, washed with water and brine, dried (Na2SO4) and concentrated. Column chromatography (SiO2; CH2Cl2) gives the title compound: MS: [M+1]+=320; TLC(CH2Cl2/EtOAc 49:1): Rf=0.42.

Aufarbeitung

  1. customThe organic phase is separated off
  2. washwashed with water and brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-4963a6315e6c473497aba41396a320b8
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08058276B2

Verknüpfte Notizen

Wird geladen…