4-Amino-6-chloropyrimidine → HCID 86686852, Verbindung
Reaktionsgleichung
Br[C:2]1[N:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)=[O:9])=[CH:4][CH:3]=1.[Cl:16][C:17]1[N:22]=[CH:21][N:20]=[C:19]([NH2:23])[CH:18]=1.CN(C1C(C2C(P(C3CCCCC3)C3CCCCC3)=CC=CC=2)=CC=CC=1)C.CC([O-])(C)C.[Na+]>C1(C)C=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Cl:16][C:17]1[N:22]=[CH:21][N:20]=[C:19]([NH:23][C:2]2[N:7]=[CH:6][C:5]([C:8]([N:10]3[CH2:15][CH2:14][O:13][CH2:12][CH2:11]3)=[O:9])=[CH:4][CH:3]=2)[CH:18]=1Komponenten
7
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 150 °C
Versuchsvorschrift
To a stirred solution of (6-bromopyridin-3-yl)(morpholino)methanone (0.75 g, 2.78 mmol) in toluene (5 mL) was added 6-chloropyrimidin-4-amine (0.43 g, 3.33 mmol), Pd2(dba)3 (100 mg, 0.3 mmol), Davephos (157 mg, 0.4 mmol) and NaOt-Bu (848 mg, 8 mmol). The mixture was stirred at 150° C. for 13 hrs under N2. The mixture was evaporated and the residue was taken up in ethyl acetate (50 mL) and H2O (20 mL). The organic phase was washed with H2O (2×20 mL) and then brine (2×20 mL) and dried over Na2SO4. After filtration and concentration, the final product (350 mg, 40%) was obtained as yellow solid. LC-MS: 320.1 [M+H]+, tR=1.306 min.
Aufarbeitung
- customThe mixture was evaporated
- washThe organic phase was washed with H2O (2×20 mL)
- dry with materialbrine (2×20 mL) and dried over Na2SO4
- filtrationAfter filtration and concentration
Quellen und Nachweise
- ORD-Eintrag
- ord-8ecc71e327bd49ab9e1f105ee9f6ffa4
- Quelldatensatz
- uspto-grants-2014_06
- Patentnummer
- US08742098B2
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