Diisopropylethylamine → HCID 16097528, compound

HRID 1641381Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:13]=[C:12]([CH:14]3[CH2:16][CH2:15]3)[NH:11][N:10]=2)[C:5]([Cl:17])=[CH:4][N:3]=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>[Cl:17][C:5]1[C:6]([NH:8][C:9]2[CH:13]=[C:12]([CH:14]3[CH2:16][CH2:15]3)[NH:11][N:10]=2)=[N:7][C:2]([NH:27][C@H:25]([C:22]2[CH:21]=[CH:20][C:19]([F:18])=[CH:24][N:23]=2)[CH3:26])=[N:3][CH:4]=1

Participants

Conditions

Temperature: 175 °C

Procedure

A mixture of 2,5-dichloro-4-(5-cyclopropyl-1H-pyrazole-3-ylamino)pyrimidine (Method 7; 0.064 g, 0.235 mmol), (S)-1-(5-fluoropyridin-2-yl)ethanamine (Method 6; 0.030 g, 0.214 mmol), and DIEA (0.045 ml, 0.257 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 (0.060 g, 75%). 1H NMR (400 MHz) 12.51 and 12.09 (s, 1H), 9.70 and 9.64 (s, 1H), 8.49 (s, 1H), 8.38 (s, 1H), 8.02 and 7.93 (b, 1H), 7.63 (m, 1H), 7.40 (m, 1H), 5.93 and 5.80 (s, 1H), 5.06 (m, 1H), 1.83 (m, 1H), 1.45 (d, J=6.8 Hz, 3H), 0.94 (m, 1H), 0.84 (m, 1H), 0.74 (m, 1H), 0.63 (m, 1H). MS: Calcd.: 373. Found: [M+H]+374.

Workup

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

Sources & evidence

ORD record: ord-f524a5cf4417491cab9f3c762eb3ff2e
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08114989B2

Reaction notes

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