Dimethyl Sulfoxide → HCID 135702870, compound

HRID 566337Notes

Reaction equation

HRID 566337 reaction equation
O[CH2:2][CH2:3][CH:4]([N:14]1[C:18]2[N:19]=[C:20]([CH2:24][C:25]3[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=3)[NH:21][C:22](=[O:23])[C:17]=2[CH:16]=[N:15]1)[CH2:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(N(CC)CC)C.CS(C)=[O:42]>ClCCl>[C:3]([CH:4]([N:14]1[C:18]2[N:19]=[C:20]([CH2:24][C:25]3[CH:26]=[CH:27][C:28]([O:31][CH3:32])=[CH:29][CH:30]=3)[NH:21][C:22](=[O:23])[C:17]=2[CH:16]=[N:15]1)[CH2:5][CH2:6][CH2:7][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)(=[O:42])[CH3:2]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 136386376HCID 136386376, compound

Product 1

HCID 135702870HCID 135702870, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

151 mg (0.35 mmol) of 1-[1-(-hydroxy-ethyl)-4-phenyl-butyl]-6-(4-methoxy-benzyl)-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one are dissolved in 1 ml of DMSO and 3.5 ml of dichloromethane, and the solution is cooled to 0° C. 0.485 ml of triethylamine and 245 mg of SO3/pyridine complex are added, and the mixture is stirred for 15 hours at room temperature. The mixture is diluted with 20 ml of dichloromethane, extracted with 1N HCl and saturated NaHCO3 solution, the extract is dried over Na2SO4, and the solvent is removed in vacuo. Purification by chromatography (PE-EA=2:1) gives 115 mg (76%), M.p.: 129° C.

Workup

  1. extractionextracted with 1N HCl and saturated NaHCO3 solution
  2. dry with materialthe extract is dried over Na2SO4
  3. customthe solvent is removed in vacuo
  4. customPurification by chromatography (PE-EA=2:1)
  5. customgives 115 mg (76%), M.p.: 129° C.

Sources & evidence

ORD record
ord-92a82c62d2a9428e99ea3e5fae3107d6
Source dataset
uspto-grants-2001_01
Patent number
US06174884B1

Reaction notes

Loading…