Diisopropylethylamine → HCID 118162090, compound

HRID 1749541Notes

Reaction equation

HRID 1749541 reaction equation
[CH3:1][C:2]1([CH3:18])[C@@H:5]([C:6]2[N:10]=[CH:9][N:8]([CH:11]3[CH2:16][CH2:15][CH2:14][CH2:13][O:12]3)[N:7]=2)[CH2:4][C@H:3]1[NH2:17].Cl[C:20]1[C:25]([C:26]#[N:27])=[CH:24][N:23]=[C:22]([S:28][CH3:29])[N:21]=1.CCN(C(C)C)C(C)C>C(O)(C)C>[CH3:1][C:2]1([CH3:18])[C@@H:5]([C:6]2[N:10]=[CH:9][N:8]([CH:11]3[CH2:16][CH2:15][CH2:14][CH2:13][O:12]3)[N:7]=2)[CH2:4][C@H:3]1[NH:17][C:20]1[C:25]([C:26]#[N:27])=[CH:24][N:23]=[C:22]([S:28][CH3:29])[N:21]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 131141834-Chloro-2-(methylsulfanyl)pyrimidine-5-carbonitrileHCID 118162079HCID 118162079, compound

Product 1

HCID 118162090HCID 118162090, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of (1R,3S)-2,2-dimethyl-3-(1-(tetrahydro-2H-pyran-2-yl)-1H-1,2,4-triazol-3-yl)cyclobutanamine (340 mg, crude) and 4-chloro-2-(methylthio)pyrimidine-5-carbonitrile (210 mg, 1.14 mmol) and DIEA (450 mg, 3.50 mmol) in isopropanol (5 mL) was stirred at 90° C. for 1 h. After removal of the solvent, the residue was purified by silica gel column chromatography (10%-30% ethyl acetate in petroleum ether) to afford the title compound (290 mg, 0.727 mmol, 65% yield for two steps). MS (ESI) m/z 400.2 [M+H]+.

Workup

  1. customAfter removal of the solvent
  2. customthe residue was purified by silica gel column chromatography (10%-30% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-28ee7748182b417ab4eed97dc7e68fa2
Source dataset
uspto-grants-2015_10
Patent number
US09156798B2

Reaction notes

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