Cyclopropanecarboxaldehyde → 4-(6-bromo-2-cyclopropyl-1H-1,3-benzodiazol-1-yl)pyrimidin-2-amine

HRID 1398508Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1398508
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[NH:9][C:10]1[CH:15]=[CH:14][N:13]=[C:12]([NH2:16])[N:11]=1.[CH:17]1([CH:20]=O)[CH2:19][CH2:18]1.OOS([O-])=O.[K+]>CN(C=O)C.CCOC(C)=O>[Br:8][C:5]1[CH:6]=[CH:7][C:2]2[N:1]=[C:20]([CH:17]3[CH2:19][CH2:18]3)[N:9]([C:10]3[CH:15]=[CH:14][N:13]=[C:12]([NH2:16])[N:11]=3)[C:3]=2[CH:4]=1

Komponenten

6

Edukt 3

HCID 123114CyclopropanecarboxaldehydeHCID 23707502Potassium hydroxy sulfiteHCID 681818104-N-(2-amino-5-bromophenyl)pyrimidine-2,4-diamine

Produkt 1

HCID 681817554-(6-bromo-2-cyclopropyl-1H-1,3-benzodiazol-1-yl)pyrimidin-2-amine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 4-N-(2-amino-5-bromophenyl)pyrimidine-2,4-diamine (400 mg, 1.43 mmol) in DMF (4 mL) were added cyclopropanecarbaldehyde (130 mg, 1.86 mmol) and oxone (527 mg, 0.86 mmol). The reaction was stirred at RT for 3 days. The mixture was diluted with EtOAc (20 mL) and washed with water. The aqueous layer was extracted with more EtOAc. The combined organics were dried over Na2SO4, filtered and concentrated in vacuo. Purification by flash chromatography (Isolute column, 100% DCM to 2% MeOH/DCM) afforded the title compound as an orange solid: 1H NMR (500 MHz, MeOD) δ 1.16-1.24 (2H, m), 1.24-1.29 (2H, m), 2.32-2.48 (1H, m), 6.98 (1H, d, J=5.36 Hz), 7.41-7.45 (1H, m), 7.47-7.52 (1H, m), 7.90 (1H, d, J=1.89 Hz), 8.51 (1H, d, J=5.20 Hz); LC-MS (Method B): m/z=+330.0, 331.8 (M+H)+.

Aufarbeitung

  1. washwashed with water
  2. extractionThe aqueous layer was extracted with more EtOAc
  3. dry with materialThe combined organics were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by flash chromatography (Isolute column, 100% DCM to 2% MeOH/DCM)

Quellen und Nachweise

ORD-Eintrag
ord-88fa5fdb471a43f99cb0a4e019655ef5
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08901313B2

Notizen zur Reaktion

Wird geladen…