2-(Tributylstannyl)furan → tert-Butyl 6-amino-4-(2-furyl)-1H-pyrazolo[3,4-d]pyrimidine-1-carboxylate

HRID 8290

Reaction equation

HRID 8290 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]2[N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[N:9]=[CH:10][C:5]2=[C:4](Cl)[N:3]=1.C([Sn](CCCC)(CCCC)[C:24]1[O:25][CH:26]=[CH:27][CH:28]=1)CCC>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[NH2:1][C:2]1[N:7]=[C:6]2[N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[N:9]=[CH:10][C:5]2=[C:4]([C:24]2[O:25][CH:26]=[CH:27][CH:28]=2)[N:3]=1

Participants

5

Reactant 2

HCID 43936882-(Tributylstannyl)furanHCID 22015553tert-butyl 6-amino-4-chloro-1H-pyrazolo[3,4-d]pyrimidine-1-carboxylate

Product 1

HCID 22015534tert-Butyl 6-amino-4-(2-furyl)-1H-pyrazolo[3,4-d]pyrimidine-1-carboxylateYield 99%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of tert-butyl 6-amino-4-chloro-1H-pyrazolo[3,4-d]pyrimidine-1-carboxylate (269 mg, 1 mmol) in DMF (2 mL) was treated with PdCl2(PPh3)2 (35 mg, 0.05 mmol) and 2-(tributylstannyl)furan (315 μL, 1 mmol), stirred at room temperature for 16 h and the resulting solid filtered and washed with EtOAc to give the title compound (298 mg, 99%) as a cream solid.

Workup

  1. filtrationthe resulting solid filtered
  2. washwashed with EtOAc

Sources & evidence

ORD record
ord-93819c7ac34e4827a4382a8241f398be
Source dataset
uspto-grants-2006_08
Patent number
US07087754B2

Linked notes

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