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Potassium Phosphate, Tribasic → Tert-butyl 4-(4-phenylpyrimidin-2-yl)piperazine-1-carboxylate

HRID 875005
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 875005
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)[N:3]=1.[C:21]1(B(O)O)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.CCOC(C)=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1>[C:21]1([C:2]2[CH:7]=[CH:6][N:5]=[C:4]([N:8]3[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]3)[N:3]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 3

HCID 62657Potassium Phosphate, TribasicHCID 66827Phenylboronic AcidHCID 46738270tert-Butyl 4-(4-chloropyrimidin-2-yl)piperazine-1-carboxylate

Produkt 1

HCID 68577436Tert-butyl 4-(4-phenylpyrimidin-2-yl)piperazine-1-carboxylateAusbeute 73,4 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 636044
1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)
Katalysator
HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysator
HCID 1140TolueneLösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
115 °C

Versuchsvorschrift

tert-Butyl 4-(4-chloropyrimidin-2-yl)piperazine-1-carboxylate (300 mg, 1.0 mmol) and phenylboronic acid (183 mg, 1.5 mmol) were dissolved in toluene (10 mL) and the solution was purged with argon for 10 min. Potassium phosphate (426 mg, 2.0 mmol) was added to the reaction mixture, followed by a catalytic amount of Pd2(dba)3 (9 mg, 0.01 mmol) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (23 mg, 0.04 mmol). The reaction mixture was then heated to 115° C. for 10 h, cooled to room temperature, diluted with EtOAc, and filtered through Celite. The organic layer was washed with water and brine, dried over anhydrous Na2SO4, and concentrated under reduced pressure. The crude product was purified by column chromatography (silica 60-120 mesh, eluent 30% EtOAc in petroleum ether) to get tert-butyl 4-(4-phenylpyrimidin-2-yl)piperazine-1-carboxylate (250 mg, yield 73%). 1H NMR (300 MHz, MeOD) δ 8.28-8.23 (m, 3H), 7.46-7.43 (m, 3H), 7.34 (m, 1H), 3.80-3.77 (m, 4H), 3.56-3.53 (m, 4H), 1.48 (s, 9H). MS (ESI) m/z: Calculated for C19H24N4O2: 340.19. found: 341.2 (M+H)+

Aufarbeitung

  1. customthe solution was purged with argon for 10 min
  2. temperaturecooled to room temperature
  3. filtrationfiltered through Celite
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by column chromatography (silica 60-120 mesh, eluent 30% EtOAc in petroleum ether)

Quellen und Nachweise

ORD-Eintrag
ord-0c2d35e705de48c09bf052df294fbd2a
Quelldatensatz
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08981084B2

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