Water → HCID 131729800, compound

HRID 1510238Notes

Reaction equation

HRID 1510238 reaction equation
[CH2:1]([C@H:8]([NH:29][C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33])[C:9](=[O:28])[N:10]1[C:18]2[C:13](=[CH:14][C:15](B3OC(C)(C)C(C)(C)O3)=[CH:16][CH:17]=2)[CH2:12][CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:38]1[CH:43]=[CH:42][N:41]=[C:40]([NH2:44])[N:39]=1.C(=O)([O-])[O-].[Na+].[Na+].O>O1CCOCC1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:32]([O:31][C:30](=[O:36])[NH:29][C@@H:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:9]([N:10]1[C:18]2[C:13](=[CH:14][C:15]([C:38]3[CH:43]=[CH:42][N:41]=[C:40]([NH2:44])[N:39]=3)=[CH:16][CH:17]=2)[CH2:12][CH2:11]1)=[O:28])([CH3:34])([CH3:35])[CH3:33]

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 2233322-Amino-4-chloropyrimidineHCID 91448988HCID 91448988, compound

Product 1

HCID 131729800HCID 131729800, compoundYield 80.8%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

To a solution of tert-butyl {(1S)-1-benzyl-2-oxo-2-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-indol-1-yl]ethyl}carbamate (672 mg) and 4-chloro-2-pyrimidinamine (265 mg) in 1,4-dioxane (10 mL) were added 2M sodium carbonate aqueous solution (2.0 mL) and tetrakis(triphenylphosphine) palladium (16 mg) and the mixture was refluxed for 3 hours under nitrogen. The mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by column chromatography on silica gel to afford tert-butyl{(1S)-2-[5-(2-aminopyrimidine-4-yl)-2,3-dihydro-1H-indol-1-yl ]-1-benzyl-2-oxoethyl}carbamate (507 mg) as a powder.

Workup

  1. temperaturethe mixture was refluxed for 3 hours under nitrogen
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-237910880f6840119835031cc3e8a2b4
Source dataset
uspto-grants-2012_07
Patent number
US08211919B2

Reaction notes

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