p-Toluenesulfonic acid → HCID 68358266, compound

HRID 1406029Notes

Reaction equation

HRID 1406029 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[C:19]([C:20](OCC)=[O:21])=[C:7]2[CH2:8][CH2:9][CH2:10][C:11]3[C:12](=[N:13][C:14]([S:17][CH3:18])=[N:15][CH:16]=3)[C:6]2=[N:5]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1COCC1>[CH3:18][S:17][C:14]1[N:15]=[CH:16][C:11]2[CH2:10][CH2:9][CH2:8][C:7]3[C:6]([C:12]=2[N:13]=1)=[N:5][N:4]1[CH2:3][CH2:2][O:1][C:20](=[O:21])[C:19]=31

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 68295188HCID 68295188, compound

Product 1

HCID 68358266HCID 68358266, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of ethyl 2-(2-hydroxyethyl)-9-(methylsulfanyl)-2,4,5,6-tetrahydropyrazolo[4′,3′:6,7]cyclohepta[1,2-d]pyrimidine-3-carboxylate 34.8 mg (0.1 mmol) in THF (3 ml) was added p-toluensulfonic acid 1.9 mg (0.01 mmol). The mixture was stirred at 60° C. for 4 hours. Upon completion, the volatiles were removed in vacuo, the residue was purified by flash chromatography eluting with EtOAc/hexane 5/5 to afford 15 mg of the title compound (50% yield).

Workup

  1. customUpon completion, the volatiles were removed in vacuo
  2. customthe residue was purified by flash chromatography
  3. washeluting with EtOAc/hexane 5/5

Sources & evidence

ORD record
ord-4a21563966554db8af1f597756e416f4
Source dataset
uspto-grants-2014_12
Patent number
US08916577B2

Reaction notes

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