Triethylamine → (S)-4-Methyl-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

HRID 75282Notes

Reaction equation

HRID 75282 reaction equation
FC(F)(F)C(O)=O.[CH3:8][N:9]1[C:17]2[C:12](=[N:13][C:14]([C@@H:24]([NH2:26])[CH3:25])=[C:15]([C:18]3[N:22]([CH3:23])[N:21]=[CH:20][CH:19]=3)[CH:16]=2)[CH:11]=[CH:10]1.Cl[C:28]1[C:33]([C:34]#[N:35])=[C:32]([CH3:36])[N:31]=[C:30]([S:37][CH3:38])[N:29]=1.CCN(CC)CC>C1COCC1>[CH3:36][C:32]1[C:33]([C:34]#[N:35])=[C:28]([NH:26][C@H:24]([C:14]2[N:13]=[C:12]3[CH:11]=[CH:10][N:9]([CH3:8])[C:17]3=[CH:16][C:15]=2[C:18]2[N:22]([CH3:23])[N:21]=[CH:20][CH:19]=2)[CH3:25])[N:29]=[C:30]([S:37][CH3:38])[N:31]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 582963084-Chloro-6-methyl-2-(methylthio)pyrimidine-5-carbonitrileHCID 86707968(S)-1-(1-Methyl-6-(1-methyl-1H-pyrazol-5-yl)-1H-pyrrolo[3,2-b]pyridin-5-yl)ethanamine 2,2,2-trifluoroacetate

Product 1

HCID 86707972(S)-4-Methyl-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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a round bottomed flask was added (S)-1-(1-methyl-6-(1-methyl-1H-pyrazol-5-yl)-1H-pyrrolo[3,2-b]pyridin-5-yl)ethanamine 2,2,2-trifluoroacetate (364 mg, 0.986 mmol) in THF (6400 μL) along with 4-chloro-6-methyl-2-(methylthio)pyrimidine-5-carbonitrile (197 mg, 0.986 mmol) and Et3N (302 μL, 2.168 mmol). The reaction mixture was stirred at room temperature overnight and was subsequently purified on silica, eluting with a gradient of EtOAc/hexanes (2:8 to 9:1) to give the title compound as a clear film (270 mg, 65.5%). ESI-MS m/z [M+H]+ calc'd for C21H22N8S 419.17; found 419.4.

Workup

  1. customwas subsequently purified on silica
  2. washeluting with a gradient of EtOAc/hexanes (2:8 to 9:1)

Sources & evidence

ORD record
ord-f835c7f765ba4d1f9bd350ead14f0627
Source dataset
uspto-grants-2014_09
Patent number
US08835420B2

Reaction notes

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