Tetrahydrofuran → HCID 118364834, compound

HRID 1478576Notes

Reaction equation

HRID 1478576 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[N:12]=[C:11]3[N:13]([CH2:16][C@H:17]4[O:22][CH2:21][CH2:20][N:19]([C:23]5[N:28]=[CH:27][C:26](B6OC(C)(C)C(C)(C)O6)=[CH:25][N:24]=5)[CH2:18]4)[N:14]=[N:15][C:10]3=[N:9][CH:8]=2)[CH:4]=[N:3]1.C1C[O:41]CC1>O>[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[N:12]=[C:11]3[N:13]([CH2:16][C@@H:17]4[CH2:18][N:19]([C:23]5[N:24]=[CH:25][C:26]([OH:41])=[CH:27][N:28]=5)[CH2:20][CH2:21][O:22]4)[N:14]=[N:15][C:10]3=[N:9][CH:8]=2)[CH:4]=[N:3]1

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 123504654HCID 123504654, compound

Product 1

HCID 118364834HCID 118364834, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(S)-2-((6-(1-methyl-1H-pyrazol-4-yl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)-4-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)pyrimidin-2-yl)morpholine 55 mg (0.11 mmol) was dissolved in THF 2 ml and H2O 2 ml, and NaBO3 16 mg (0.16 mmol) was added, followed by stirring at room temperature for 2 hours. After the completion of the reaction, the reaction mixture was extracted with H2O, EA, and brine, followed by drying (Na2SO4), filtration, and concentration under reduced pressure, and the residue was purified by column chromatography (MeOH:MC=1:10), to give (S)-2-(2-((6-(1-methyl-1H-pyrazol-4-yl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)morpholino)pyrimidin-5-ol 29 mg (two steps: 67%).

Workup

  1. customAfter the completion of the reaction
  2. extractionthe reaction mixture was extracted with H2O, EA, and brine
  3. customby drying
  4. filtration(Na2SO4), filtration, and concentration under reduced pressure
  5. customthe residue was purified by column chromatography (MeOH:MC=1:10)

Sources & evidence

ORD record
ord-c44825aa95a54995adf9166871f0259e
Source dataset
uspto-grants-2016_08
Patent number
US09403831B2

Reaction notes

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