Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 136341299, compound

HRID 1506137Notes

Reaction equation

HRID 1506137 reaction equation
[Si]([O:8][CH:9]1[CH2:14][CH2:13][CH:12]([C:15]2[N:16]=[N:17][N:18]3[C:23]=2[C:22]2[CH:24]=[CH:25][NH:26][C:21]=2[N:20]=[CH:19]3)[CH2:11][CH2:10]1)(C(C)(C)C)(C)C.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>ClCCl.CO>[C:15]1([CH:12]2[CH2:11][CH2:10][CH:9]([OH:8])[CH2:14][CH2:13]2)[N:16]=[N:17][N:18]2[C:23]=1[C:22]1[CH:24]=[CH:25][NH:26][C:21]=1[N:20]=[CH:19]2

Participants

5

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 136341300HCID 136341300, compound

Product 1

HCID 136341299HCID 136341299, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

1-{4-[(tert-Butyldimethylsilyl)oxy]cyclohexyl}-7H-pyrrolo[3,2-e][1,2,3]triazolo[1,5-c]pyrimidine (500 mg, 1.35 mmol) in a mixture of dichloromethane (5 mL) and methanol (5 mL) was stirred with pyridinium p-toluenesulfonate (338 mg, 1.35 mmol) at 60° C. for 3 hours. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1→1/1 (v/v)-ethyl acetate) to give the title compound as a colorless solid (259 mg, yield 75%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1→1/1 (v/v)-ethyl acetate)

Sources & evidence

ORD record
ord-9b35f07a3fb84202a6d66e63886886f5
Source dataset
uspto-grants-2015_12
Patent number
US09216999B2

Reaction notes

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