Diisopropylethylamine → HCID 178458635, compound

HRID 415394Notes

Reaction equation

HRID 415394 reaction equation
[F:1][C:2]1[CH:3]=[N:4][C:5]([CH:8]([NH2:10])[CH3:9])=[N:6][CH:7]=1.Cl[C:12]1[N:17]=[C:16]([NH:18][C:19]2[CH:23]=[C:22]([O:24][CH:25]([CH3:27])[CH3:26])[NH:21][N:20]=2)[C:15]([Cl:28])=[CH:14][N:13]=1.CCN(C(C)C)C(C)C>CCCCO>[Cl:28][C:15]1[C:16]([NH:18][C:19]2[CH:23]=[C:22]([O:24][CH:25]([CH3:27])[CH3:26])[NH:21][N:20]=2)=[N:17][C:12]([NH:10][CH:8]([C:5]2[N:6]=[CH:7][C:2]([F:1])=[CH:3][N:4]=2)[CH3:9])=[N:13][CH:14]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 509948141-(5-Fluoropyrimidin-2-yl)ethan-1-amineHCID 178458614HCID 178458614, compound

Product 1

HCID 178458635HCID 178458635, compoundYield 27.3%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
160 °C

Procedure

A microwave reaction vessel was charged with 1-(5-fluoropyrimidin-2-yl)ethanamine (Method 1, 0.25 g, 1.77 mmol), 2,5-dichloro-N-(5-isopropoxy-1H-pyrazol-3-yl)pyrimidin-4-amine (Method 2, 0.50 g, 1.77 mmol), and DIPEA (0.30 g, 2.34 mmol). Anhydrous n-BuOH (2 ml) was added, and the tube was sealed and heated in a microwave reactor at 160° C. for 10 hours. The reaction mixture was purified by silica gel chromatography twice (by ISCO Combiflash with gradient EtOAc and DCM) to afford the title compound as a white solid (0.19 g, 27%). LC-MS, 393 (M+1). 1H NMR (CDCl3) δ 8.50 (s, 2H), 7.75 (s, 1H), 5.50 (s, 1H), 5.20 (m, 1H), 4.68 (m, 1H), 1.55 (d, 3H), 1.20 (d, 6H).

Workup

  1. customA microwave reaction vessel
  2. customthe tube was sealed
  3. customThe reaction mixture was purified by silica gel chromatography twice (by ISCO Combiflash with gradient EtOAc and DCM)

Sources & evidence

ORD record
ord-3c797034d70c4c5eb6c0d29926557428
Source dataset
uspto-grants-2012_01
Patent number
US08088784B2

Reaction notes

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