Diisopropylethylamine → HCID 11957745, compound

HRID 1641380Notes

Reaction equation

[Br:1][C:2]1[C:3]([NH:9][C:10]2[NH:14][N:13]=[C:12]([CH:15]3[CH2:17][CH2:16]3)[CH:11]=2)=[N:4][C:5](Cl)=[N:6][CH:7]=1.[F:18][C:19]1[CH:20]=[CH:21][C:22]([C@@H:25]([NH2:27])[CH3:26])=[N:23][CH:24]=1.CCN(C(C)C)C(C)C>CCCCO>[Br:1][C:2]1[C:3]([NH:9][C:10]2[CH:11]=[C:12]([CH:15]3[CH2:17][CH2:16]3)[NH:13][N:14]=2)=[N:4][C:5]([NH:27][C@H:25]([C:22]2[CH:21]=[CH:20][C:19]([F:18])=[CH:24][N:23]=2)[CH3:26])=[N:6][CH:7]=1

Participants

Conditions

Temperature: 175 °C

Procedure

A mixture of 5-bromo-2-chloro-N-(3-cyclopropyl-1H-pyrazol-5-yl)pyrimidin-4-amine (Method 8; 0.062 g, 0.196 mmol), (S)-1-(5-fluoropyridin-2-yl)ethanamine (Method 6; 0.025 g, 0.178 mmol), and DIEA (0.04 ml, 0.214 mmol) in n-BuOH (2 ml) was heated in a sealed tube at 175° C. for 20 hours. The solvent was removed under reduced pressure and the residue was purified by column chromatography (hexane:EtOAc=1:1) to give the title compound as a white solid (0.064 g, 86%). 1H NMR (400 MHz) 12.48 and 12.09 (s, 1H), 9.32 (s, 1H), 8.48 (d, J=2.4 Hz, 1H), 8.00 (b, 1H), 7.92 (s, 1H), 7.64 (m, 1H), 7.41 (m, 1H), 5.94 and 5.85 (b, 1H), 5.06 (m, 1H), 1.84 (m, 1H), 1.45 (d, J=7.2 Hz, 3H), 0.95 (m, 1H), 0.86 (m, 1H), 0.74 (m, 1H), 0.63 (m, 1H). MS: Calcd.: 417. Found: [M+H]+418.

Workup

customThe solvent was removed under reduced pressure
customthe residue was purified by column chromatography (hexane:EtOAc=1:1)

Sources & evidence

ORD record: ord-9431fb9faf9748d591d322335e21b0cd
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08114989B2

Reaction notes

Loading…