Water → HCID 70981147, compound

HRID 2280755Notes

Reaction equation

HRID 2280755 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.[CH:12]1([C:15]([NH2:18])([CH3:17])[CH3:16])[CH2:14][CH2:13]1.CCN(C(C)C)C(C)C.O>CN(C=O)C>[CH:12]1([C:15]([NH:18][C:2]2[C:7]([C:8]#[N:9])=[CH:6][N:5]=[C:4]([S:10][CH3:11])[N:3]=2)([CH3:17])[CH3:16])[CH2:14][CH2:13]1

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 558546HCID 558546, compoundHCID 131141834-Chloro-2-(methylsulfanyl)pyrimidine-5-carbonitrile

Product 1

HCID 70981147HCID 70981147, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 4-chloro-2-(methylthio)pyrimidine-5-carbonitrile (750 mg, 4.0 mmol) in DMF (8 mL) was added 2-cyclopropylpropan-2-amine (400 mg, 4.0 mmol) and DIEA (1560 mg, 12.0 mmol). The resulting mixture was stirred at 60° C. for 2 h. Water was added and the mixture was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated to give the crude product, which was purified by silica gel column chromatography (0-30% ethyl acetate in petroleum ether) to afford the title compound (665 mg, 2.68 mmol, 66% yield) as a white solid. MS (ESI) m/z=249.2 [M+H]+.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. customto give the crude product, which
  7. customwas purified by silica gel column chromatography (0-30% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-3dddbee9700d45048b64aa5f2251847e
Source dataset
uspto-grants-2015_09
Patent number
US09139534B2

Reaction notes

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