Sodium Chloride → HCID 57929464, compound

HRID 2280758Notes

Reaction equation

HRID 2280758 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.[CH:21]1([NH2:25])[CH2:24][CH2:23][CH2:22]1.[Cl-].[Na+]>CN(C=O)C>[CH:21]1([NH:25][C:2]2[C:7]([C:8]#[N:9])=[CH:6][N:5]=[C:4]([S:10][CH3:11])[N:3]=2)[CH2:24][CH2:23][CH2:22]1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 75645CyclobutylamineHCID 81531DiisopropylethylamineHCID 131141834-Chloro-2-(methylsulfanyl)pyrimidine-5-carbonitrile

Product 1

HCID 57929464HCID 57929464, compoundYield 71.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a stirring solution of 4-chloro-2-(methylthio)pyrimidine-5-carbonitrile (2 g, 10.8 mmol) in DMF (10 mL) was added DIEA (4.2 g, 32.4 mmol) and cyclobutanamine (2.3 g, 32.4 mmol) at 0° C. The resulting mixture was stirred at 60° C. for 2 h. The reaction mixture was poured into saturated sodium chloride, and extracted with ethyl acetate three times. The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated to afford the crude product. The crude product was purified via silica gel column chromatography (10% ethyl acetate in petroleum ether) to get the desired product as a white solid (1.7 g, 7.7 mmol, 71% yield). MS (ESI) m/z=221.2[M+H]+.

Workup

  1. extractionextracted with ethyl acetate three times
  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 via silica gel column chromatography (10% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-e98cb99f4d154c62b8f739daa07ace6c
Source dataset
uspto-grants-2015_09
Patent number
US09139534B2

Reaction notes

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