Pyridine → HCID 11996259, compound

HRID 655857Notes

Reaction equation

HRID 655857 reaction equation
N[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]3=[N:13][CH:14]=[N:15][C:16]([NH2:17])=[C:11]3[CH:10]=[N:9]2)=[CH:4][CH:3]=1.[CH2:18]([S:22](Cl)(=[O:24])=[O:23])[CH2:19][CH2:20][CH3:21].[N:26]1C=CC=CC=1.CN(C=O)C>CO>[NH2:17][C:16]1[N:15]=[CH:14][N:13]=[C:12]2[N:8]([C:5]3[CH:4]=[C:3]([NH:26][S:22]([CH2:18][CH2:19][CH2:20][CH3:21])(=[O:24])=[O:23])[CH:2]=[CH:7][CH:6]=3)[N:9]=[CH:10][C:11]=12

Participants

6

Reactant 4

HCID 1049PyridineHCID 6228DimethylformamideHCID 754301-Butanesulfonyl chlorideHCID 119959601-(4-Amino-phenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-ylamine

Product 1

HCID 11996259HCID 11996259, compoundYield 44.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Title compound 11A, 1-(4-amino-phenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-ylamine (40 mg, 1.0 eq, 0.18 mmol), 1-butanesulphonylchloride (23 μl, 1.0 eq, 0.18 mmol) and pyridine (14 μl, 1.0 eq, 0.18 mmol) were added to DMF (1 ml) and the mixture was stirred for 42 hours at room temperature under an inert atmosphere. Methanol was then added (1 ml) and the solvents were removed in vacuo. The resultant residue was absorbed onto silica and purified by column chromatography using DCM/MeOH (96:4) as eluent to yield the title compound as a white solid (27 mg, 0.08 mmol, 44%). LCMS: [M+H]+=347, Rt=1.58 min, 100% purity.

Workup

  1. customthe solvents were removed in vacuo
  2. customThe resultant residue was absorbed onto silica
  3. custompurified by column chromatography

Sources & evidence

ORD record
ord-8a9e94756c4049c68f91b2091bef06bb
Source dataset
uspto-grants-2011_12
Patent number
US08071607B2

Reaction notes

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