[6-(Methylsulfinyl)-4-pyrimidinyl]acetonitrile → [6-({[2-(Trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]methyl}amino)-4-pyrimidinyl]acetonitrile

HRID 2401223Notes

Reaction equation

HRID 2401223 reaction equation
CS([C:4]1[N:9]=[CH:8][N:7]=[C:6]([CH2:10][C:11]#[N:12])[CH:5]=1)=O.[F:13][C:14]([F:27])([F:26])[C:15]1[NH:25][C:18]2=[N:19][CH:20]=[C:21]([CH2:23][NH2:24])[CH:22]=[C:17]2[CH:16]=1>C(O)(C)C.C(#N)C.CS(C)=O>[F:27][C:14]([F:13])([F:26])[C:15]1[NH:25][C:18]2=[N:19][CH:20]=[C:21]([CH2:23][NH:24][C:4]3[N:9]=[CH:8][N:7]=[C:6]([CH2:10][C:11]#[N:12])[CH:5]=3)[CH:22]=[C:17]2[CH:16]=1

Participants

6

Reactant 2

HCID 67111377[6-(Methylsulfinyl)-4-pyrimidinyl]acetonitrile2×HCID 671114591H-Pyrrolo[2,3-b]pyridine-5-methanamine, 2-(trifluoromethyl)-2×

Product 1

HCID 51355873[6-({[2-(Trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]methyl}amino)-4-pyrimidinyl]acetonitrileYield 8.4%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 3776IsopropanolSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of [6-(methylsulfinyl)-4-pyrimidinyl]acetonitrile (Intermediate 16, 150 mg, 0.828 mmol) and 1-[2-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]methanamine (Intermediate 5, 178 mg, 0.828 mmol) in isopropanol (7 mL) was stirred and heated at 80° C. overnight. The reaction mixture was cooled to room temperature and condensed. This solid was dissolved in a mixture of acetonitrile and DMSO (1:1) (2.7 mL) and purified by MDAP (3 injections). Fractions containing the suspected product were combined and concentrated under reduced pressure. The solid was dissolved in a mixture of acetonitrile and DMSO (1:1) (1.8 mL) and purified again by MDAP (2 injections). Fractions containing the suspected product were combined and concentrated under reduced pressure to give the title compound as a solid (23 mg);

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customcondensed
  3. custompurified by MDAP (3 injections)
  4. additionFractions containing the suspected product
  5. concentrationconcentrated under reduced pressure
  6. dissolutionThe solid was dissolved in a mixture of acetonitrile and DMSO (1:1) (1.8 mL)
  7. custompurified again by MDAP (2 injections)
  8. additionFractions containing the suspected product
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9d72a881b07642888a97df947162342b
Source dataset
uspto-grants-2014_08
Patent number
US08796283B2

Reaction notes

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