Diisopropylethylamine → HCID 178461874, compound

HRID 415407Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:13]=[C:12]([N:14]([CH3:16])[CH3:15])[NH:11][N:10]=2)[C:5]([F:17])=[CH:4][N:3]=1.Cl.[F:19][C:20]1[CH:21]=[N:22][C:23]([C@@H:26]([NH2:28])[CH3:27])=[N:24][CH:25]=1.CCN(C(C)C)C(C)C>CCCCO>[CH3:15][N:14]([CH3:16])[C:12]1[NH:11][N:10]=[C:9]([NH:8][C:6]2[C:5]([F:17])=[CH:4][N:3]=[C:2]([NH:28][C@H:26]([C:23]3[N:24]=[CH:25][C:20]([F:19])=[CH:21][N:22]=3)[CH3:27])[N:7]=2)[CH:13]=1

Participants

Conditions

Temperature: 160 °C

Procedure

A microwave reaction vessel was charged with N3-(2-chloro-5-fluoropyrimidin-4-yl)-N5,N5-dimethyl-1H-pyrazole-3,5-diamine (Method 35, 50 mg, 0.2 mmol), (S)-1-(5-fluoropyrimidin-2-yl)ethanamine hydrochloride (Method 7, 50 mg, 0.23 mmol), and DIPEA (0.15 ml, 0.86 mmol) in n-BuOH (1 ml) was heated in a microwave reactor at 160° C. for 2 hours. Solvent was removed. The residue was purified by silica gel chromatography (by ISCO Combiflash with gradient 0-5% Methanol in methylene chloride with 1% NH4OH) to afford the title compound as a white solid (49 mg, 67%). 1H NMR (CD3OD, 400 MHz) δ 8.77 (s, 2H), 8.23 (s, 1H), 5.32 (br, 1H), 3.92 (q, 1H), 3.13 (s, 6H), 1.71 (d, 3H); m/z 362

Workup

customA microwave reaction vessel
customSolvent was removed
customThe residue was purified by silica gel chromatography (by ISCO Combiflash with gradient 0-5% Methanol in methylene chloride with 1% NH4OH)

Sources & evidence

ORD record: ord-2d6f6ec64d4a4f28b8f074b602461805
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08088784B2

Reaction notes

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