Potassium Phosphate, Tribasic → HCID 178488539, Verbindung

HRID 2169221Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2169221
[C:1]([O:5][C:6]([C:8]1[C:13]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:12]([OH:22])[N:11]=[C:10]([CH2:23][C:24]2[CH:29]=[C:28]([O:30][CH3:31])[CH:27]=[CH:26][C:25]=2Br)[N:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:33]1(B(O)O)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C(O)CCC.O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd]>[C:1]([O:5][C:6]([C:8]1[C:13]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:12]([OH:22])[N:11]=[C:10]([CH2:23][C:24]2[CH:29]=[C:28]([O:30][CH3:31])[CH:27]=[CH:26][C:25]=2[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[N:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

7

Edukt 4

HCID 62657Potassium Phosphate, TribasicHCID 66827Phenylboronic AcidHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 178488296tert-butyl 2-[(2-bromo-5-methoxyphenyl)methyl]-4-oxo-5-phenylmethoxy-1H-pyrimidine-6-carboxylate

Produkt 1

HCID 178488539HCID 178488539, VerbindungAusbeute 56,94 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumKatalysatorHCID 22253497Water butanolLösungsmittel

Versuchsvorschrift

To a stirred solution of 5-benzyloxy-2-(2-bromo-5-methoxybenzyl)-6-hydroxypyrimidine-4-carboxylic acid tert-butyl ester (138) (3 g, 5.988 mmol) in n-butanol:water (3:1, 12 mL) were added phenyl boronic acid (1.096 g, 8.982 mmol), X-Phos (427 mg, 0.898 mmol), K3PO4 (4.44 g, 20.958 mmol) and Pd(dba)2 (275 mg, 0.479 mmol). The reaction mixture was refluxed for 10 h. After completion of the reaction, the mixture was evaporated to get a crude product which was purified by a normal silica column using 2% methanol in dichloromethane to afford 5-benzyloxy-6-hydroxy-2-(4-methoxybiphenyl-2-ylmethyl)-pyrimidine-4-carboxylic acid tert-butyl ester (139) (1.7 g, 56.94%) as an off-white solid.

Aufarbeitung

  1. temperatureThe reaction mixture was refluxed for 10 h
  2. customAfter completion of the reaction
  3. customthe mixture was evaporated
  4. customto get a crude product which
  5. customwas purified by a normal silica column

Quellen und Nachweise

ORD-Eintrag
ord-84d8c9c281ee4dbeaf5be15e439850ea
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09045486B2

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