Diisopropylethylamine → HCID 178461869, compound

HRID 415408Notes

Reaction equation

HRID 415408 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]([Cl: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>[Cl:17][C:5]1[C:6]([NH:8][C:9]2[CH:13]=[C:12]([N:14]([CH3:16])[CH3:15])[NH:11][N:10]=2)=[N:7][C:2]([NH:28][C@H:26]([C:23]2[N:24]=[CH:25][C:20]([F:19])=[CH:21][N:22]=2)[CH3:27])=[N:3][CH:4]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 66624037(S)-1-(5-Fluoropyrimidin-2-yl)ethanamine hydrochlorideHCID 178482926HCID 178482926, compound

Product 1

HCID 178461869HCID 178461869, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
160 °C

Procedure

A microwave reaction vessel was charged with N3-(2,5-dichloropyrimidin-4-yl)-N5,N5-dimethyl-1H-pyrazole-3,5-diamine (Method 36, 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 DCM with 1% NH4OH) to afford the title compound as a white solid. 1H NMR (CD3OD, 400 MHz) δ 8.77 (s, 2H), 8.26 (br, 1H), 5.35 (br, 1H), 3.49 (q, 1H), 3.11 (s, 6H), 1.72 (d, 3H); m/z 378.

Workup

  1. customA microwave reaction vessel
  2. customSolvent was removed
  3. customThe residue was purified by silica gel chromatography (by ISCO Combiflash with gradient 0-5% methanol in DCM with 1% NH4OH)

Sources & evidence

ORD record
ord-8d5a024804c540e7bd926cf214613cf0
Source dataset
uspto-grants-2012_01
Patent number
US08088784B2

Reaction notes

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