Sodium borohydride → HCID 71558825, compound

HRID 400879Notes

Reaction equation

HRID 400879 reaction equation
[C:1]([C:5]1[N:6]=[C:7]([N:23]2[CH2:27][CH2:26][C:25]([F:29])([F:28])[CH2:24]2)[C:8]2[N:13]=[N:12][N:11]([CH2:14][C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[O:16])[C:9]=2[N:10]=1)([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>CO>[C:1]([C:5]1[N:6]=[C:7]([N:23]2[CH2:27][CH2:26][C:25]([F:28])([F:29])[CH2:24]2)[C:8]2[N:13]=[N:12][N:11]([CH2:14][CH:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[OH:16])[C:9]=2[N:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 71558675HCID 71558675, compound

Product 1

HCID 71558825HCID 71558825, compoundYield 38.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2-(5-tert-butyl-7-(3,3-difluoropyrrolidin-1-yl)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl)-1-phenylethanone (6.0 mg, 15.0 μmol) and NaBH4 (1.7 mg, 45.0 μmol) in methanol (250 μL) was stirred at the room temperature for 1 h. The reaction mixture was directly purified by preparative HPLC (column: Gemini Sum C18 110A 75×30 mm. mobile phase: water (0.05% Et3N): acetonitrile 72:25% to 5:95%. WL: 230 nm Flow: 30 mL/min.) to afford the title compound as white solid (2.3 mg, 38%). MS (m/e): 403.4 (MH+).

Workup

  1. customThe reaction mixture was directly purified by preparative HPLC (column: Gemini Sum C18 110A 75×30 mm. mobile phase: water (0.05% Et3N): acetonitrile 72:25% to 5:95%. WL: 230 nm Flow: 30 mL/min.)

Sources & evidence

ORD record
ord-3179ec55db4e46439e83127ee5264f13
Source dataset
uspto-grants-2014_06
Patent number
US08741906B2

Reaction notes

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