Potassium Carbonate → HCID 11582016、化合物

HRID 387468ノート

反応式

HRID 387468 の反応式
[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

参加物

7

反応物 4

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

生成物 1

HCID 11582016HCID 11582016、化合物収率 12.4%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-43eb2bc5968e4a10bb32ddeac41074b0
出典データセット
uspto-grants-2013_02
特許番号
US08372971B2

反応ノート

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