Acetonitrile → (S)-4-Amino-6-((1-(1-methyl-6-(1-methyl-1H-pyrazol-5-yl)-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)amino)-2-(methylsulfonyl)pyrimidine-5-carbonitrile

HRID 75281Notes

Reaction equation

HRID 75281 reaction equation
[NH2:1][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[N:27]([CH3:28])[N:26]=[CH:25][CH:24]=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>[NH2:1][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[N:27]([CH3:28])[N:26]=[CH:25][CH:24]=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 86707970(S)-4-Amino-6-((1-(1-methyl-6-(1-methyl-1H-pyrazol-5-yl)-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)amino)-2-(methylthio)pyrimidine-5-carbonitrile

Product 1

HCID 86707971(S)-4-Amino-6-((1-(1-methyl-6-(1-methyl-1H-pyrazol-5-yl)-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)amino)-2-(methylsulfonyl)pyrimidine-5-carbonitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a round-bottomed flask was added (S)-4-amino-6-((1-(1-methyl-6-(1-methyl-1H-pyrazol-5-yl)-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)amino)-2-(methylthio)pyrimidine-5-carbonitrile (200 mg, 0.477 mmol) in acetonitrile (5418 μL) and water (5418 μL). The mixture was cooled to 0° C. Oxone® (733 mg, 1.192 mmol) was added to give an orange solution. The reaction mixture was stirred at 0° C. for 30 min and then allowed to warm to room temperature. After 2 h, LCMS showed the reaction to be complete. The reaction mixture was subsequently diluted with EtOAc and washed with brine (3×). The combined organic layers were dried over Na2SO4, filtered, and concentrated to give the title compound as a yellow solid. ESI-MS m/z [M+H]+ calc'd for C20H21N9O2S, 452.15; found 452.4.

Workup

  1. customto give an orange solution
  2. temperatureto warm to room temperature
  3. waitAfter 2 h
  4. customthe reaction
  5. washwashed with brine (3×)
  6. dry with materialThe combined organic layers were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-988e67ddc54e48f59e74bf15799a32c8
Source dataset
uspto-grants-2014_09
Patent number
US08835420B2

Reaction notes

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