Acetonitrile → HCID 178434490, compound

HRID 75300Notes

Reaction equation

HRID 75300 reaction equation
[CH3:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([NH:10][C@H:11]([C:13]2[N:18]=[C:17]3[CH:19]=[CH:20][N:21]([CH3:22])[C:16]3=[CH:15][C:14]=2[C:23]2[C:24]([CH3:28])=[N:25][NH:26][CH:27]=2)[CH3:12])[N:5]=[C:4](SC)[N:3]=1.O[O:32][S:33]([O-:35])=O.[K+].[C:37](#N)C>O.CCOC(C)=O>[CH3:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([NH:10][C@H:11]([C:13]2[N:18]=[C:17]3[CH:19]=[CH:20][N:21]([CH3:22])[C:16]3=[CH:15][C:14]=2[C:23]2[C:24]([CH3:28])=[N:25][NH:26][CH:27]=2)[CH3:12])[N:5]=[C:4]([S:33]([CH3:37])(=[O:35])=[O:32])[N:3]=1

Participants

6

Reactant 3

HCID 6342AcetonitrileHCID 23707502Potassium hydroxy sulfiteHCID 178503445HCID 178503445, compound

Product 1

HCID 178434490HCID 178434490, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a round-bottomed flask was added a mixture of (S)-4-methyl-6-((1-(1-methyl-6-(3-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)amino)-2-(methylthio)pyrimidine-5-carbonitrile (100 mg, 0.239 mmol) in acetonitrile (7 mL) and water (7 mL). The reaction mixture was cooled to 0° C. Oxone (367 mg, 0.597 mmol) was added and the reaction mixture was stirred at 0° C. for 30 minutes and then allowed to warm to RT. After 1.5 hours the reaction mixture was diluted with EtOAc and washed with H2O (3×). The combined organic layers were dried over Na2SO4, filtered, and concentrated to give the title compound as a yellow solid, which was used without further purification. ESI-MS m/z [M+H]+ calc'd for C21H22N8O2S, 451; found 451.

Workup

  1. additionTo a round-bottomed flask was added
  2. temperatureto warm to RT
  3. washwashed with H2O (3×)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ef08754072474158bbede2190f305328
Source dataset
uspto-grants-2014_09
Patent number
US08835420B2

Reaction notes

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