Dimethyl Sulfoxide → HCID 67300355, compound

HRID 589181Notes

Reaction equation

HRID 589181 reaction equation
FC(F)(F)C(O)=O.FC(F)(F)C(O)=O.FC(F)(F)C(O)=O.[NH2:22][C:23]1[N:28]2[N:29]=[CH:30][C:31]([C:32]3[CH:33]=[CH:34][C:35]([C:38]([OH:41])([CH3:40])[CH3:39])=[N:36][CH:37]=3)=[C:27]2[N:26]=[C:25]([CH:42]2[CH2:48][CH:47]3[NH:49][CH:44]([CH2:45][CH2:46]3)[CH2:43]2)[C:24]=1I.[CH3:51][S:52]([O-:54])=[O:53].[Na+].CS(C)=O>[Cu]I>[NH2:22][C:23]1[N:28]2[N:29]=[CH:30][C:31]([C:32]3[CH:33]=[CH:34][C:35]([C:38]([OH:41])([CH3:40])[CH3:39])=[N:36][CH:37]=3)=[C:27]2[N:26]=[C:25]([CH:42]2[CH2:48][CH:47]3[NH:49][CH:44]([CH2:45][CH2:46]3)[CH2:43]2)[C:24]=1[S:52]([CH3:51])(=[O:54])=[O:53]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 2733271Sodium methanesulfinateHCID 86674908HCID 86674908, compound

Product 1

HCID 67300355HCID 67300355, compoundYield 82.1%

Reagents, catalysts & solvents 1

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst

Procedure

2-{5-[7-amino-5-(8-azabicyclo[3.2.1]oct-3-yl)-6-iodopyrazolo[1,5-a]pyrimidin-3-yl]pyridin-2-yl}propan-2-ol tris(trifluoroacetate) (salt) (0.720 g, 0.851 mmol), sodium methanesulfinate (306 mg, 2.55 mmol), and Copper(I) iodide (486 mg, 2.55 mmol) were dissolved/suspended in dry dimethyl sulfoxide (18 mL, 250 mmol) under a nitrogen atmosphere. The reaction was placed in an oil bath at 90° C. After mixing 15 min, HPLC showed the starting material to have been consumed and a mixture of the desired material:des-iodo material was observed. The reaction mixture was poured into a 7:3 mixture of sat'd NH4Cl:20% NH4OH (200 ml) and extracted 3×75 ml with 10% IPA in DCM. The combined organics were washed with brine, dried, filtered and evaporated to provide a yellow oil, which was purified by silica gel chromatography, eluted with 0-15% (10% NH4OH in MeOH) in chloroform to provide the desired material as a yellow solid (319 mg).

Workup

  1. customThe reaction was placed in an oil bath at 90° C
  2. additionAfter mixing 15 min
  3. customto have been consumed
  4. additiona mixture of the desired material
  5. additionThe reaction mixture was poured into a 7:3 mixture of sat'd NH4Cl
  6. extraction20% NH4OH (200 ml) and extracted 3×75 ml with 10% IPA in DCM
  7. washThe combined organics were washed with brine
  8. customdried
  9. filtrationfiltered
  10. customevaporated
  11. customto provide a yellow oil, which
  12. customwas purified by silica gel chromatography
  13. washeluted with 0-15% (10% NH4OH in MeOH) in chloroform

Sources & evidence

ORD record
ord-9293b482ad46495d8d73343dc107ec05
Source dataset
uspto-grants-2016_01
Patent number
US09227971B2

Reaction notes

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