Sodium Bicarbonate → HCID 21874781, compound

HRID 750528Notes

Reaction equation

HRID 750528 reaction equation
Cl[C:2]1[C:3]2[N:11]=[N:10][N:9]([CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-:21])=[O:20])[CH:14]=3)[C:4]=2[N:5]=[C:6]([NH2:8])[N:7]=1.[CH3:22][Si:23]([CH3:37])([CH3:36])[CH2:24][CH2:25][O:26][CH2:27][N:28]1[C:32](B(O)O)=[CH:31][CH:30]=[N:29]1.C([O-])(O)=O.[Na+]>C1COCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[N+:19]([C:15]1[CH:14]=[C:13]([CH:18]=[CH:17][CH:16]=1)[CH2:12][N:9]1[C:4]2[N:5]=[C:6]([NH2:8])[N:7]=[C:2]([C:32]3[N:28]([CH2:27][O:26][CH2:25][CH2:24][Si:23]([CH3:37])([CH3:36])[CH3:22])[N:29]=[CH:30][CH:31]=3)[C:3]=2[N:11]=[N:10]1)([O-:21])=[O:20]

Participants

7

Reactant 3

HCID 516892Sodium BicarbonateHCID 21874590HCID 21874590, compoundHCID 21874652(1-((2-(Trimethylsilyl)ethoxy)methyl)-1H-pyrazol-5-yl)boronic acid

Product 1

HCID 21874781HCID 21874781, compoundYield 34%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 7-chloro-3-(3-nitrobenzyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidine-5-amine (306 mg, 1 mmol), 1-(2-(trimethylsilyl)ethoxymethyl)-1H-pyrazol-5-ylboronic acid (2 mmol), Pd(PPh3)4 (100 mg) and saturated NaHCO3 (5 mL) in THF (20 mL) was refluxed for 2 h, diluted with water (20 mL), extracted with EtOAc(2×20 mL), dried (MgSO4), concentrated in vacuo and purified by chromatography [SiO2; CH2Cl2:EtOAc (6:1)] to give 3-(3-nitrobenzyl)-7-(1-(2-(trimethylsilyl)ethoxymethyl)-1H-pyrazol-5-yl)-3H-[1,2,3]triazolo[4,5-d]pyrimidine-5-amine (156 mg, 34%) as a pale yellow syrup.

Workup

  1. extractionextracted with EtOAc(2×20 mL)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. custompurified by chromatography [SiO2; CH2Cl2:EtOAc (6:1)]

Sources & evidence

ORD record
ord-0aedbbe8dae04ae5b5d809419a96d6c1
Source dataset
uspto-grants-2008_07
Patent number
US07405219B2

Reaction notes

Loading…