Potassium Carbonate → 6-(4-{5-[(3-Chlorophenyl)amino]-1,3,4-oxadiazol-2-yl}phenoxy) pyrimidine-2,4-diamine

HRID 1994047Notes

Reaction equation

HRID 1994047 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[O:13][C:12]([C:14]3[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=3)=[N:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1.C[Si]([N-][Si](C)(C)C)(C)C.[K+].Cl[C:32]1[N:37]=[C:36]([NH2:38])[N:35]=[C:34]([NH2:39])[CH:33]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CO>[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[O:13][C:12]([C:14]3[CH:19]=[CH:18][C:17]([O:20][C:32]4[N:37]=[C:36]([NH2:38])[N:35]=[C:34]([NH2:39])[CH:33]=4)=[CH:16][CH:15]=3)=[N:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 674322,4-Diamino-6-chloropyrimidineHCID 3251421Potassium bis(trimethylsilyl)amideHCID 1361796964-[5-(3-Chloro-phenylamino)-[1,3,4]oxadiazol-2-yl]-phenol

Product 1

HCID 116109376-(4-{5-[(3-Chlorophenyl)amino]-1,3,4-oxadiazol-2-yl}phenoxy) pyrimidine-2,4-diamineYield 31.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

4-{5-[(3-chlorophenyl)amino]-1,3,4-oxadiazol-2-yl}phenol (143.8 mg, 0.5 mmol) was dissolved in 3 mL of anhydrous DMF in a 2-5 mL microwave vial (Personal Chemistry). Solid potassium bis(trimethylsilyl)amide (200.0 mg, 1.0 mmol) was added and the reaction mixture was stirred with heating at 80° C. for 10 min, then 6-chloro-2,4-diamino-pyrimidine (86.7 mg, 0.6 mmol) was added, followed by anhydrous K2CO3 (69.1 mg, 0.5 mmol). Then the vial was capped and microwaved at 180° C. for 40 min. Then the reaction mixture was diluted with ca. 1 mL of MeOH, filtered through 0.22 um syringe filter and purified by reverse-phase preparative HPLC in acetonitrile/water system with 0.01% TFA. Fractions, containing the product, were partitioned between ca. 50 mL of EtOAc and ca. 50 mL of saturated aqueous NaHCO3. EtOAc layer was washed with brine, dried over anhydrous Na2SO4 and filtered. Solvent was removed in vacuo to give the title product as a light-yellow solid (62.0 mg). Yield 31.3%.

Workup

  1. customThen the vial was capped
  2. custommicrowaved at 180° C. for 40 min
  3. filtrationfiltered through 0.22 um syringe
  4. filtrationfilter
  5. custompurified by reverse-phase preparative HPLC in acetonitrile/water system with 0.01% TFA
  6. additionFractions, containing the product
  7. customwere partitioned between ca. 50 mL of EtOAc and ca. 50 mL of saturated aqueous NaHCO3
  8. washEtOAc layer was washed with brine
  9. dry with materialdried over anhydrous Na2SO4
  10. filtrationfiltered
  11. customSolvent was removed in vacuo

Sources & evidence

ORD record
ord-900663e711834eac9b7d6a6ce7ae1b4e
Source dataset
uspto-grants-2010_01
Patent number
US07652051B2

Reaction notes

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