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3-Iodo-2,5-dimethyl-7-(pentan-3-yl)pyrazolo[1,5-a]pyrimidine → 3-(3-Methyl-thiophene-2-yl)-7-(1-ethyl-propyl)-2,5-dimethyl-pyrazolo[1,5-a]pyrimidine

HRID 1639657
ノート
印刷プレビュー

反応式

HRID 1639657 の反応式
[Br-].[CH3:2][C:3]1[CH:7]=[CH:6][S:5][C:4]=1[Zn+].[CH2:9]([CH:11]([C:14]1[N:19]2[N:20]=[C:21]([CH3:24])[C:22](I)=[C:18]2[N:17]=[C:16]([CH3:25])[CH:15]=1)[CH2:12][CH3:13])[CH3:10]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C1COCC1>[CH3:2][C:3]1[CH:7]=[CH:6][S:5][C:4]=1[C:22]1[C:21]([CH3:24])=[N:20][N:19]2[C:14]([CH:11]([CH2:9][CH3:10])[CH2:12][CH3:13])=[CH:15][C:16]([CH3:25])=[N:17][C:18]=12
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 248985233-Iodo-2,5-dimethyl-7-(pentan-3-yl)pyrazolo[1,5-a]pyrimidineHCID 178429658HCID 178429658、化合物

生成物 1

HCID 248987423-(3-Methyl-thiophene-2-yl)-7-(1-ethyl-propyl)-2,5-dimethyl-pyrazolo[1,5-a]pyrimidine

試薬・触媒・溶媒 2

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 8028
Tetrahydrofuran
溶媒

反応条件

温度
100 °C

実験手順

Charge an oven dried flask with 3-methyl-2-thienylzinc bromide (11.0 mL, 5.5 mmol), anhydrous THF (6.0 mL) and 7-(1-ethyl-propyl)-3-iodo-2,5-dimethyl-pyrazolo[1,5-a]pyrimidine (0.536 g, 1.56 mmol). Degas for 10-15 min with positive argon pressure and add dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium (II) dichloromethane (0.12 g, 0.15 mmol). Reflux overnight in an oil bath (100° C.) under an inert atmosphere. Cool the reaction to room temperature, quench with saturated ammonium chloride, and dilute with ethyl acetate (75 mL). Separate and extract the aqueous portion with ethyl acetate (50 mL). Combine the organic phases, dry over anhydrous magnesium sulfate, filter, and concentrate under reduced pressure. Purify the resulting residue using flash chromatography, eluting with 100% pentane/0% (25% ethyl acetate/pentane) to 0% pentane/100% (25% ethyl acetate/pentane) in a step gradient of 10% increments to give a white foam. Triturate with hexane and filter. (0.432 g, 8%). 1H NMR (400 MHz, CDCl3): 7.26 (d, J=4.8, MHz, 1H), 6.96 (d, J=5.3 Hz, 1H), 6.42 (s, 1H), 3.64-3.60 (m, 1H), 2.53 (s, 3H), 2.43 (s, 3H), 2.14 (s, 3H), 1.87-1.79 (m, 4H), 0.88 (t, J=7.0 Hz, 6H).

後処理

  1. additionCharge an oven
  2. customDegas for 10-15 min with positive argon pressure
  3. temperatureCool
  4. customthe reaction to room temperature
  5. customquench with saturated ammonium chloride
  6. additiondilute with ethyl acetate (75 mL)
  7. customSeparate
  8. extractionextract the aqueous portion with ethyl acetate (50 mL)
  9. dry with materialCombine the organic phases, dry over anhydrous magnesium sulfate
  10. filtrationfilter
  11. concentrationconcentrate under reduced pressure
  12. customPurify the resulting residue
  13. washeluting with 100% pentane/0% (25% ethyl acetate/pentane) to 0% pentane/100% (25% ethyl acetate/pentane) in a step gradient of 10% increments
  14. customto give a white foam
  15. customTriturate with hexane
  16. filtrationfilter

出典と根拠

ORDレコード
ord-ed85291c60714ed2bce19877ebc9ad50
出典データセット
uspto-grants-2012_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08110580B2

反応ノート

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