Methanol → HCID 178507925, compound

HRID 661400Notes

Reaction equation

HRID 661400 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]1[CH:4]=[C:5]([NH:9][C:10]2[NH:11][C:12]([C:15]3[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=3)=[N:13][N:14]=2)[CH:6]=[CH:7][CH:8]=1.C([O-])([O-])=O.[Cs+].[Cs+].Cl[C:31]1[CH:36]=[C:35]([NH2:37])[N:34]=[C:33]([NH2:38])[N:32]=1.CO>O1CCOCC1>[F:23][C:2]([F:22])([F:1])[C:3]1[CH:4]=[C:5]([NH:9][C:10]2[NH:11][C:12]([C:15]3[CH:20]=[CH:19][C:18]([O:21][C:31]4[N:32]=[C:33]([NH2:38])[N:34]=[C:35]([NH2:37])[CH:36]=4)=[CH:17][CH:16]=3)=[N:13][N:14]=2)[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 10796Cesium carbonateHCID 674322,4-Diamino-6-chloropyrimidineHCID 178515914HCID 178515914, compound

Product 1

HCID 178507925HCID 178507925, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

4-(5-{[3-(trifluoromethyl)phenyl]amino}-4H-1,2,4-triazol-3-yl)phenol (160 mg, 0.5 mmol) was dissolved in 3 mL of anhydrous dioxane in 2-5 mL microwave vial (Personal Chemistry). Solid Cs2CO3 (163.0 mg, 0.5 mmol) was added, followed by 4-chloro-2,6,-diaminopyrimidine (79.5 mg, 0.55 mmol). The vial was capped and microwaved at 200° C. for 20 min. Then ca. 3 mL of MeOH was added to dissolve the formed suspension, the solution was transferred into a round-bottom flask and solvent was removed in vacuo. The residue was re-dissolved in 3 mL of DMF, filtered through 0.22 u syringe filter and purified by reverse phase preparative HPLC using acetonitrile/water system with 0.01% of TFA.

Workup

  1. customThe vial was capped
  2. custommicrowaved at 200° C. for 20 min
  3. dissolutionto dissolve the formed suspension
  4. customthe solution was transferred into a round-bottom flask
  5. customsolvent was removed in vacuo
  6. dissolutionThe residue was re-dissolved in 3 mL of DMF
  7. filtrationfiltered through 0.22 u syringe
  8. filtrationfilter
  9. custompurified by reverse phase preparative HPLC

Sources & evidence

ORD record
ord-bffc62c02c924af6ae848992a485d2d5
Source dataset
uspto-grants-2011_12
Patent number
US08084618B2

Reaction notes

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