Potassium Acetate → HCID 25255096, compound

HRID 1692805Notes

Reaction equation

HRID 1692805 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)[C:5]2[S:10][C:9]([N:11]([CH3:19])[CH:12]3[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]3)=[N:8][C:6]=2[N:7]=1.[NH2:26][C:27]1[CH:32]=[CH:31][C:30](B2OC(C)(C)C(C)(C)O2)=[CH:29][N:28]=1.C([O-])(=O)C.[K+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(#N)C>[NH2:26][C:27]1[N:28]=[CH:29][C:30]([C:2]2[N:3]=[C:4]([N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)[C:5]3[S:10][C:9]([N:11]([CH3:19])[CH:12]4[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]4)=[N:8][C:6]=3[N:7]=2)=[CH:31][CH:32]=1

Participants

6

Reactant 3

HCID 517044Potassium AcetateHCID 27565555-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amineHCID 866300855-Chloro-N-methyl-N-(1-methylpiperidin-4-yl)-7-morpholinothiazolo[4,5-d]pyrimidin-2-amine

Product 1

HCID 25255096HCID 25255096, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6342AcetonitrileSolvent

Procedure

5-Chloro-N-methyl-N-(1-methylpiperidin-4-yl)-7-morpholinothiazolo[4,5-d]pyrimidin-2-amine, 2-aminopyridine-5-boronic acid pinacol ester (2 eq), and trans-dichlorobis(triphenylphosphine)palladium(II) (0.1 eq) were slurried with equal parts 1M potassium acetate (3 eq) and acetonitrile. The solution was microwaved at 140° C. for 10 minutes. The solvent was removed in vacuo and the resulting precipitate was purified by reverse phase silica gel chromatography to give the product 144.

Workup

  1. customThe solution was microwaved at 140° C. for 10 minutes
  2. customThe solvent was removed in vacuo
  3. customthe resulting precipitate was purified by reverse phase silica gel chromatography

Sources & evidence

ORD record
ord-a7332d226fab4c05a60c8820780adf20
Source dataset
uspto-grants-2012_04
Patent number
US08158626B2

Reaction notes

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