Water → HCID 86724353, compound

HRID 2274282Notes

Reaction equation

HRID 2274282 reaction equation
CS(O[CH2:6][CH:7]([OH:43])[C:8]([NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([NH:17][C:18]2[C:23]([F:24])=[CH:22][N:21]=[C:20]([NH:25][C:26]3[CH:31]=[CH:30][C:29]([O:32][CH2:33][CH2:34][O:35][Si:36]([C:39]([CH3:42])([CH3:41])[CH3:40])([CH3:38])[CH3:37])=[CH:28][CH:27]=3)[N:19]=2)[CH:12]=1)=[O:9])(=O)=O.[H-].[Na+].C(Cl)(Cl)Cl.CO.O>C1COCC1>[Si:36]([O:35][CH2:34][CH2:33][O:32][C:29]1[CH:28]=[CH:27][C:26]([NH:25][C:20]2[N:19]=[C:18]([NH:17][C:13]3[CH:12]=[C:11]([NH:10][C:8]([CH:7]4[CH2:6][O:43]4)=[O:9])[CH:16]=[CH:15][CH:14]=3)[C:23]([F:24])=[CH:22][N:21]=2)=[CH:31][CH:30]=1)([C:39]([CH3:40])([CH3:42])[CH3:41])([CH3:37])[CH3:38]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 21584188Chloroform methanolHCID 86724354HCID 86724354, compound

Product 1

HCID 86724353HCID 86724353, compoundYield 78.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-((3-((2-((4-(2-((tert-butyldimethylsilyl)oxy)ethoxy)phenyl)amino)-5-fluoropyrimidin-4-yl)amino)phenyl)amino)-2-hydroxy-3-oxopropyl methanesulfonate (0.240 g) in THF was added NaH (0.018 g) and the reaction mixture was stirred at room temperature for 30 min. The reaction was monitored on TLC using CHCl3:methanol (9:1) as mobile phase. After completion, the reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was dried over sodium sulfate and the solvent was removed under reduced pressure. The crude material was purified by Combiflash, and the product eluted with 1.6% methanol in CHCl3 to give 0.16 g of N-(3-((2-((4-(2-((tert-butyldimethylsilyl)oxy)ethoxy)phenyl)amino)-5-fluoropyrimidin-4-yl)amino)phenyl)oxirane-2-carboxamide.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. customthe solvent was removed under reduced pressure
  4. customThe crude material was purified by Combiflash
  5. washthe product eluted with 1.6% methanol in CHCl3

Sources & evidence

ORD record
ord-0a99b4a92bae4442ad8f64825f1a33df
Source dataset
uspto-grants-2015_09
Patent number
US09126950B2

Reaction notes

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