Sodium Iodide → HCID 71245107, compound

HRID 574000Notes

Reaction equation

HRID 574000 reaction equation
C[Si](Cl)(C)C.[I-].[Na+].[F:8][C:9]1[CH:10]=[CH:11][C:12]([C@@H:15]([NH:17][C:18]2[C:23]([CH3:24])=[CH:22][N:21]=[C:20]([NH:25][C:26]3[C:27]([O:32]C)=[N:28][CH:29]=[CH:30][CH:31]=3)[N:19]=2)[CH3:16])=[N:13][CH:14]=1>C(#N)C>[F:8][C:9]1[CH:10]=[CH:11][C:12]([C@@H:15]([NH:17][C:18]2[C:23]([CH3:24])=[CH:22][N:21]=[C:20]([NH:25][C:26]3[C:27](=[O:32])[NH:28][CH:29]=[CH:30][CH:31]=3)[N:19]=2)[CH3:16])=[N:13][CH:14]=1

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 71245086HCID 71245086, compound

Product 1

HCID 71245107HCID 71245107, compoundYield 101.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

Trimethylsilyl chloride (0.20 mL, 1.58 mmol) and sodium iodide (235 mg, 1.57 mmol) were added to a stirred solution of (S)—N4-(1-(5-fluoropyridin-2-yl)ethyl)-N2-(2-methoxypyridin-3-yl)-5-methylpyrimidine-2,4-diamine (Preparation 2b, 185 mg, 0.52 mmol) in acetonitrile (5 mL) and the mixture was stirred and heated at 80° C. for 45 min. After cooling to ambient temperature, the mixture was concentrated and treated with saturated aqueous sodium thiosulphate solution. After stirring for 10 minutes, the precipitate was filtered, washed with water and diethyl ether and dried to give the title compound (179 mg, 100%) as a solid.

Workup

  1. temperatureAfter cooling to ambient temperature
  2. concentrationthe mixture was concentrated
  3. additiontreated with saturated aqueous sodium thiosulphate solution
  4. stirringAfter stirring for 10 minutes
  5. filtrationthe precipitate was filtered
  6. washwashed with water and diethyl ether
  7. customdried

Sources & evidence

ORD record
ord-bba4d03a9c95499f8908425582e348d2
Source dataset
uspto-grants-2015_05
Patent number
US09034311B2

Reaction notes

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