4-(Morpholinomethyl)aniline → 5-Methyl-N2-(4-morpholin-4-ylmethyl-phenyl)-pyrimidine-2,4-diamine

HRID 1095035

Reaktionsgleichung

Cl[C:2]1[N:7]=[C:6]([NH2:8])[C:5]([CH3:9])=[CH:4][N:3]=1.[N:10]1([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([NH2:23])=[CH:19][CH:18]=2)[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1>C(O)(=O)C>[CH3:9][C:5]1[C:6]([NH2:8])=[N:7][C:2]([NH:23][C:20]2[CH:19]=[CH:18][C:17]([CH2:16][N:10]3[CH2:11][CH2:12][O:13][CH2:14][CH2:15]3)=[CH:22][CH:21]=2)=[N:3][CH:4]=1

Komponenten

Reaktionsbedingungen

Temperatur: 70 °C

Versuchsvorschrift

A mixture of 2-chloro-5-methyl-pyrimidin-4-ylamine (0.40 g, 2.8 mmol) and 4-morpholin-4-ylmethyl-phenylamine (0.60 g, 3.1 mmol) in acetic acid (15 mL) was heated at 70° C. for 17 h. After cooling to room temperature, the mixture was concentrated. The residue was taken in water (30 mL) and neutralized with 10% NaOH solution until pH˜10. The resulting aqueous layer was extracted with EtOAc (2×30 mL) and the combined organic layers washed with brine, dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated to afford the title compound as a brown syrup (0.70 g, 83%). It was used in the next step without purification. MS (ES+): m/z 300 (M+H)+

Aufarbeitung

temperatureAfter cooling to room temperature
concentrationthe mixture was concentrated
extractionThe resulting aqueous layer was extracted with EtOAc (2×30 mL)
washthe combined organic layers washed with brine
dry with materialdried over anhydrous Na2SO4
filtrationfiltered
concentrationThe filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag: ord-85f8f3efd8ee4a208fbe796f9b435fbc
Quelldatensatz: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08133900B2

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