Water → 4-bromo-6-methoxy-N-[4-(1-methylindol-3-yl)pyrimidin-2-yl]benzene-1,3-diamine

N-(4-Bromo-2-methoxy-5-nitrophenyl)-4-(1-methylindol-3-yl)pyrimidin-2-amine (Intermediate 145, 1.074 g, 2.36 mmol), iron (0.792 g, 14.19 mmol) and NH4Cl (95 mg, 1.77 mmol) were heated at reflux in ethanol (39 mL) and water (13 mL) for 1.5 h. The mixture was then cooled and concentrated in vacuo. The resulting residue was triturated in 10% CH3OH in CH2Cl2 (30 mL) for 15 minutes and the mixture was then filtered. The residues were triturated again with 10% CH3OH in CH2Cl2 (30 mL) and the mixture then filtered. The combined filtrates were washed with brine, dried (MgSO4) and concentrated in vacuo. Purification by FCC, eluting with CH2Cl2 gave the title compound (0.937 g, 93%) as a cream foam; 1H NMR: 3.79 (3H, s), 3.89 (3H, s), 4.86 (2H, s), 7.06 (1H, s), 7.18-7.30 (3H, m), 7.54 (1H, d), 7.83 (1H, s), 7.87 (1H, s), 8.33 (1H, d), 8.35 (1H, s), 8.43 (1H, d); m/z: ES+ MH+ 424/426.

1. temperatureThe mixture was then cooled
2. concentrationconcentrated in vacuo
3. customThe resulting residue was triturated in 10% CH3OH in CH2Cl2 (30 mL) for 15 minutes
4. filtrationthe mixture was then filtered
5. customThe residues were triturated again with 10% CH3OH in CH2Cl2 (30 mL)
6. filtrationthe mixture then filtered
7. washThe combined filtrates were washed with brine
8. dry with materialdried (MgSO4)
9. concentrationconcentrated in vacuo
10. customPurification by FCC
11. washeluting with CH2Cl2

ORD-Eintrag

ord-9369c0cebf1c4912983a2d3e35184535

Quelldatensatz

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08946235B2