Water → HCID 118364834, compound

HRID 1478574Notes

Reaction equation

HRID 1478574 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.[OH2:38]>C1COCC1>[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:38])=[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 962WaterHCID 123504654HCID 123504654, compound

Product 1

HCID 118364834HCID 118364834, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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 109 mg (0.22 mmol) was dissolved in THF 3 ml and distilled water 3 ml, and NaBO3 65 mg (0.651 mmol) was added. The mixture was stirred at room temperature for 1 hour. When the reaction was completed, the reaction mixture was extracted with MC and water, and the organic layer was dried over Na2SO4. Prep LC with 4% MeOH/MC gave a product 54 mg (63%).

Workup

  1. additionwas added
  2. extractionthe reaction mixture was extracted with MC and water
  3. dry with materialthe organic layer was dried over Na2SO4

Sources & evidence

ORD record
ord-02871738307c45ef8bd0b24df6e4698c
Source dataset
uspto-grants-2016_08
Patent number
US09403831B2

Reaction notes

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