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

HRID 75298Notes

Reaction equation

HRID 75298 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:24]=[CH:25][S:26][CH:27]=2)[CH3:12])[N:5]=[C:4](SC)[N:3]=1.O[O:31][S:32]([O-:34])=O.[K+].[C:36](#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:24]=[CH:25][S:26][CH:27]=2)[CH3:12])[N:5]=[C:4]([S:32]([CH3:36])(=[O:34])=[O:31])[N:3]=1

Participants

6

Reactant 3

HCID 6342AcetonitrileHCID 23707502Potassium hydroxy sulfiteHCID 86707988(S)-4-Amino-6-((1-(1-methyl-6-(thiazol-4-yl)-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)amino)-2-(methylthio)pyrimidine-5-carbonitrile

Product 1

HCID 86707990(S)-4-amino-6-((1-(1-methyl-6-(thiazol-4-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 a mixture of (S)-4-amino-6-((1-(1-methyl-6-(thiazol-4-yl)-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)amino)-2-(methylthio)pyrimidine-5-carbonitrile (22 mg, 0.052 mmol) in acetonitrile (7 mL) and water (7 mL). The reaction mixture was cooled to 0° C. and Oxone (80 mg, 0.130 mmol) was added. The reaction mixture was stirred at 0° C. for 30 minutes and was 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 C19H18N8O2S2, 455; found 455.

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-85bfdac3c7a54e2db8d6aca6af10ddc9
Source dataset
uspto-grants-2014_09
Patent number
US08835420B2

Reaction notes

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