Water → HCID 71245075, compound

HRID 573988Notes

Reaction equation

HRID 573988 reaction equation
C[Si](Cl)(C)C.[I-].[Na+].[Si:8]([O:15][CH:16]1[CH2:21][CH2:20][N:19]([C:22]2[N:27]=[C:26]([NH:28][C:29]3[C:30]([O:35]C)=[N:31][CH:32]=[CH:33][CH:34]=3)[N:25]=[C:24]([NH:37][C@H:38]([C:40]3[CH:45]=[CH:44][C:43]([F:46])=[CH:42][N:41]=3)[CH3:39])[CH:23]=2)[CH2:18][CH2:17]1)([C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:10])[CH3:9].O>C(#N)C>[Si:8]([O:15][CH:16]1[CH2:21][CH2:20][N:19]([C:22]2[CH:23]=[C:24]([NH:37][C@H:38]([C:40]3[CH:45]=[CH:44][C:43]([F:46])=[CH:42][N:41]=3)[CH3:39])[N:25]=[C:26]([NH:28][C:29]3[C:30](=[O:35])[NH:31][CH:32]=[CH:33][CH:34]=3)[N:27]=2)[CH2:18][CH2:17]1)([C:11]([CH3:14])([CH3:12])[CH3:13])([CH3:10])[CH3:9]

Participants

6

Reactant 4

HCID 962WaterHCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 71245121HCID 71245121, compound

Product 1

HCID 71245075HCID 71245075, compoundYield 128.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

Trimethylsilyl chloride (0.285 mL, 2.25 mmol) and sodium iodide (337 mg, 2.25 mmol) were added to a stirred solution of 6-(4-{[tert-butyl(dimethyl)silyl]oxy}piperidin-1-yl)-N4-[(1S)-1-(5-fluoropyridin-2-yl)ethyl]-N2-(2-methoxypyridin-3-yl)pyrimidine-2,4-diamine (Preparation 10c, 415 mg, 0.75 mmol) in acetonitrile (5 mL) and the reaction mixture was heated at 80° C. for 4.5 hours. After cooling to ambient temperature, water was added and the mixture was extracted with ethyl acetate (×3). The pH was then adjusted to ca. 6 with 2M aqueous sodium hydroxide solution and the aqueous phase was extracted with ethyl acetate (×3). The combined organic extract was washed with water and brine, dried (MgSO4), filtered and the solvent evaporated under reduced pressure to give the title compound (0.52 g, 100%) as a brown oil which was used in the next synthetic step without further purification.

Workup

  1. temperatureAfter cooling to ambient temperature
  2. extractionthe mixture was extracted with ethyl acetate (×3)
  3. extractionthe aqueous phase was extracted with ethyl acetate (×3)
  4. extractionThe combined organic extract
  5. washwas washed with water and brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-83a8bce9571a4ec2bef740915574df55
Source dataset
uspto-grants-2015_05
Patent number
US09034311B2

Reaction notes

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