Tetrahydrofuran → HCID 86724352, compound

HRID 2274281Notes

Reaction equation

HRID 2274281 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19]2[N:24]=[C:23]([NH:25][C:26]3[CH:27]=C(NC(=O)C=C)C=[CH:30][CH:31]=3)[C:22]([F:37])=[CH:21][N:20]=2)=[CH:14][CH:13]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C[N+:39]1([O-])[CH2:44][CH2:43][O:42][CH2:41][CH2:40]1.C(Cl)(Cl)Cl.C[OH:51].C1[CH2:56][O:55]CC1>O.O=[Os](=O)(=O)=O>[Si:1]([O:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19]2[N:24]=[C:23]([NH:25][C:26]3[CH:27]=[C:44]([NH:39][C:40](=[O:51])[CH:41]([OH:42])[CH2:56][OH:55])[CH:43]=[CH:30][CH:31]=3)[C:22]([F:37])=[CH:21][N:20]=2)=[CH:14][CH:13]=1)([C:4]([CH3:6])([CH3:5])[CH3:7])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 82029Methyl morpholine oxideHCID 21584188Chloroform methanolHCID 86724351HCID 86724351, compound

Product 1

HCID 86724352HCID 86724352, compound

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent

Procedure

Into a 25 mL 3-neck RBF equipped with a calcium chloride guard tube, N-(3-((2-((4-(2-((tert-butyldimethylsilyl)oxy)ethoxy)phenyl)amino)-5-fluoropyrimidin-4-yl)amino)phenyl)acrylamide (2.0 g), in THF (15 mL), NMO (0.671 g) and OsO4 (4.85 mL 4% in water) solution were charged at room temperature. The reaction mixture was stirred at room temperature for 2 hr. The reaction was monitored on TLC using CHCl3:methanol (9:1). After completion, the reaction mixture was poured in water and extracted into ethyl acetate. The organic layer was washed with water, dried over sodium sulfate and concentrated under reduced pressure at 40° C. Crude material was purified by Combiflash chromatography eluted with 1.9% methanol in CHCl3 to give 2.0 g of N-(3-((2-((4-(2-((tert-butyldimethylsilyl)oxy)ethoxy)phenyl)amino)-5-fluoropyrimidin-4-yl)amino)phenyl)-2,3-dihydroxypropanamide.

Workup

  1. customInto a 25 mL 3-neck RBF equipped with a calcium chloride guard tube
  2. extractionextracted into ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure at 40° C
  6. customCrude material was purified by Combiflash chromatography
  7. washeluted with 1.9% methanol in CHCl3

Sources & evidence

ORD record
ord-b1403d6414dd4393a19fcd663fe29939
Source dataset
uspto-grants-2015_09
Patent number
US09126950B2

Reaction notes

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