Potassium Carbonate → HCID 11582016, 화합물

HRID 387468노트

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HRID 387468 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([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:4][CH:3]=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]=[CH:4][C:5]([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:6][CH:7]=1

참가 물질

7

반응물 4

HCID 11430Potassium CarbonateHCID 674322,4-Diamino-6-chloropyrimidineHCID 3251421Potassium bis(trimethylsilyl)amideHCID 136041855HCID 136041855, 화합물

생성물 1

HCID 11582016HCID 11582016, 화합물수율 12.4%

시약·촉매·용매 2

HCID 887Methanol용매HCID 6228Dimethylformamide용매

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온도
80 °C

실험 절차

4-{5-[(4-chlorophenyl)amino]-1,3,4-oxadiazol-2-yl}phenol (144.0 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 (100.0 mg, 0.5 mmol) was added and the reaction mixture was stirred with heating at 80° C. for 10 min, then 6-chloro-2,4-diamino-pyrimidine (72.3 mg, 0.5 mmol) was added, followed by anhydrous K2CO3 (34.5 mg, 0.25 mmol). Then the vial was capped and microwaved at 200° C. for 15 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. 40 mL of EtOAc and ca. 40 mL of saturated 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 beige solid (24.5 mg).

후처리

  1. customThen the vial was capped
  2. custommicrowaved at 200° C. for 15 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. 40 mL of EtOAc and ca. 40 mL of saturated NaHCO3
  8. washEtOAc layer was washed with brine
  9. dry with materialdried over anhydrous Na2SO4
  10. filtrationfiltered
  11. customSolvent was removed in vacuo

출처 및 근거

ORD 기록
ord-43eb2bc5968e4a10bb32ddeac41074b0
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08372971B2

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