Ethanol → HCID 118162165, compound

HRID 1749439Notes

Reaction equation

HRID 1749439 reaction equation
[CH3:1]O.Cl.Cl[C:5]1[C:10]([C:11]#[N:12])=[CH:9][N:8]=[C:7]([S:13][CH3:14])[N:6]=1.[CH3:15][CH2:16][N:17](C(C)C)C(C)C.C([O:27][CH2:28][CH3:29])(=O)C.[CH2:30](O)[CH3:31]>>[OH:27][CH2:28][C@H:29]1[CH2:15][C@@H:16]([NH:17][C:5]2[C:10]([C:11]#[N:12])=[CH:9][N:8]=[C:7]([S:13][CH3:14])[N:6]=2)[C:30]1([CH3:31])[CH3:1]

Participants

6

Reactant 5

HCID 702EthanolHCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 131141834-Chloro-2-(methylsulfanyl)pyrimidine-5-carbonitrileHCID 21893726Hydrochloride methanol

Product 1

HCID 118162165HCID 118162165, compoundYield 96%

Conditions

Temperature
40 °C

Procedure

The compound isolated above, 3-amino-2,2-dimethylcyclobutyl)MeOH hydrochloride (1.0 equiv.) and 4-chloro-2-(methylthio)pyrimidine-5-carbonitrile (1.0 equiv.) were dissolved in DIEA (3.0 equiv.) and ethanol (0.4 M). The solution was heated to 40° C. for 1 h. The reaction was concentrated under reduced pressure and the yellow residue purified via biotage chromatography (0-60% ethyl acetate in hexanes, then 60% ethyl acetate in hexanes) to afford the title compound (96% yield). MS(ESI) m/z 278.6[M]+.

Workup

  1. customThe compound isolated above
  2. concentrationThe reaction was concentrated under reduced pressure
  3. customthe yellow residue purified via biotage chromatography (0-60% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-f8f46c33844c4bf6a3ca8c4b20998cdc
Source dataset
uspto-grants-2015_10
Patent number
US09156798B2

Reaction notes

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