Diisopropylethylamine → HCID 118162209, compound

HRID 1749430Notes

Reaction equation

HRID 1749430 reaction equation
Cl[C:2]1[N:7]=[C:6]([Cl:8])[C:5]([C:9]#[N:10])=[CH:4][N:3]=1.[CH2:11]([C:13]1[C:18]([CH2:19][NH2:20])=[CH:17][N:16]=[CH:15][N:14]=1)[CH3:12].CCN(C(C)C)C(C)C>C(O)(C)C>[Cl:8][C:6]1[C:5]([C:9]#[N:10])=[CH:4][N:3]=[C:2]([NH:20][CH2:19][C:18]2[C:13]([CH2:11][CH3:12])=[N:14][CH:15]=[N:16][CH:17]=2)[N:7]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 140269072,4-Dichloro-5-cyanopyrimidineHCID 82418513HCID 82418513, compound

Product 1

HCID 118162209HCID 118162209, compoundYield 11.4%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a mixture of 2,4-dichloropyrimidine-5-carbonitrile (1.0 equiv. 61.4) and (4-ethylpyrimidin-5-yl)methanamine (1.0 equiv.) in isopropanol (0.2 M) was added DIEA (2.0 equiv.). The mixture was stirred at room temperature under nitrogen overnight. The reaction mixture was extracted with ethyl acetate, the organic layer was washed with a solution of ammonium chloride and concentrated under vacuum to give crude product, which was purified by silica gel chromatography (30% ethyl acetate in petroleum ether) to afford the title compound (11.4% yield) as brown solid. 1H-NMR (400 MHz, CD3OD) δ (ppm) 9.95 (d, J=3.2 Hz, 1H), 8.64 (d, J=12.0 Hz, 1H), 8.58 (d, J=19.6 Hz, 1H), 4.70 (d, J=20.4 Hz, 2H), 2.97-2.87 (m, 2H), 1.33-1.27 (m, 3H); MS (ESI) m/z 275.1 [M+H]+.

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate
  2. washthe organic layer was washed with a solution of ammonium chloride
  3. concentrationconcentrated under vacuum
  4. customto give crude product, which
  5. customwas purified by silica gel chromatography (30% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-05311a5b711e4ea0ac2ce19097b58e7f
Source dataset
uspto-grants-2015_10
Patent number
US09156798B2

Reaction notes

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