2-Chloro-5-methylpyrimidin-4-amine → 5-Methyl-N2-(4-(2-(pyrrolidin-1-yl)ethoxy)phenyl)pyrimidine-2,4-diamine

HRID 1095033

Reaktionsgleichung

Reaktionsgleichung von HRID 1095033
Cl[C:2]1[N:7]=[C:6]([NH2:8])[C:5]([CH3:9])=[CH:4][N:3]=1.[N:10]1([CH2:15][CH2:16][O:17][C:18]2[CH:23]=[CH:22][C:21]([NH2:24])=[CH:20][CH:19]=2)[CH2:14][CH2:13][CH2:12][CH2:11]1>C(O)(=O)C>[CH3:9][C:5]1[C:6]([NH2:8])=[N:7][C:2]([NH:24][C:21]2[CH:22]=[CH:23][C:18]([O:17][CH2:16][CH2:15][N:10]3[CH2:14][CH2:13][CH2:12][CH2:11]3)=[CH:19][CH:20]=2)=[N:3][CH:4]=1

Komponenten

4

Edukt 2

HCID 43021752-Chloro-5-methylpyrimidin-4-amineHCID 64937494-(2-(Pyrrolidin-1-yl)ethoxy)aniline

Produkt 1

HCID 576750855-Methyl-N2-(4-(2-(pyrrolidin-1-yl)ethoxy)phenyl)pyrimidine-2,4-diamineAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

A mixture of 2-chloro-5-methyl-pyrimidin-4-ylamine (0.50 g, 3.5 mmol) and 4-(2-pyrrolidin-1-yl-ethoxy)-phenylamine (1.1 g, 5.3 mmol) in acetic acid (8 mL) was sealed in a microwave reaction tube and irradiated with microwave at 150° C. for 15 min. After cooling to room temperature, the cap was removed and the mixture 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 grey solid (0.80 g, 73%). It was used in the next step without purification. MS (ES+): m/z 314 (M+H)+.

Aufarbeitung

  1. customwas sealed in a microwave reaction tube
  2. customirradiated with microwave at 150° C. for 15 min
  3. customthe cap was removed
  4. concentrationthe mixture concentrated
  5. extractionThe resulting aqueous layer was extracted with EtOAc (2×30 mL)
  6. washthe combined organic layers washed with brine
  7. dry with materialdried over anhydrous Na2SO4
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-8d6388e6487847ccbfd9896bd0a2692e
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08133900B2

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