Water → HCID 71237256, compound

HRID 2280820Notes

Reaction equation

HRID 2280820 reaction equation
Cl[C:2]1[C:7]([C:8]#[N:9])=[CH:6][N:5]=[C:4]([S:10][CH3:11])[N:3]=1.CCN(C(C)C)C(C)C.Cl.[CH2:22]([C:24]1([NH2:29])[CH2:28][CH2:27][CH2:26][CH2:25]1)[CH3:23].O>CS(C)=O>[CH2:22]([C:24]1([NH:29][C:2]2[C:7]([C:8]#[N:9])=[CH:6][N:5]=[C:4]([S:10][CH3:11])[N:3]=2)[CH2:28][CH2:27][CH2:26][CH2:25]1)[CH3:23]

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 131141834-Chloro-2-(methylsulfanyl)pyrimidine-5-carbonitrileHCID 755307821-ethylcyclopentanamine hydrochloride

Product 1

HCID 71237256HCID 71237256, compoundYield 60.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
60 °C

Procedure

To a stirring solution of 4-chloro-2-(methylthio)pyrimidine-5-carbonitrile (984 mg, 5.3 mmol) in DMSO (10 mL) was added DIEA (2.1 g, 15.9 mmol) and 1-ethylcyclopentanamine hydrochloride (900 mg crude). The resulting mixture was stirred at 60° C. for 2 h. The reaction mixture was poured into water and extracted with ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated to afford the crude product. The crude product was purified by silica gel column chromatography (5% ethyl acetate in petroleum ether) to get the desired product as a yellow oil (830 mg, 3.2 mmol, 53.5% yield). MS (ESI) m/z=263.2 [M+H]+.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto afford the crude product
  6. customThe crude product was purified by silica gel column chromatography (5% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-d62c4f3c37324659966aa59ceb24fe94
Source dataset
uspto-grants-2015_09
Patent number
US09139534B2

Reaction notes

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