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Dimethylformamide → 3,6-diethyl-N-(1-ethylpropyl)-5-(5,6,7,8-tetrahydronaphthalen-2-yl)pyrazin-2-amine

HRID 1063259
ノート
印刷プレビュー

反応式

HRID 1063259 の反応式
FC(F)(F)S(O[C:7]1[C:16]([C:17]2[C:22]([CH2:23][CH3:24])=[N:21][C:20]([NH:25][CH:26]([CH2:29][CH3:30])[CH2:27][CH3:28])=[C:19]([CH2:31][CH3:32])[N:18]=2)=[CH:15][C:14]2[CH2:13][CH2:12][CH2:11][CH2:10][C:9]=2[CH:8]=1)(=O)=O.CN(C=O)C.C([SiH](CC)CC)C>C(OCC)(=O)C.O.C1(PCCCPC2C=CC=CC=2)C=CC=CC=1>[CH2:31]([C:19]1[C:20]([NH:25][CH:26]([CH2:29][CH3:30])[CH2:27][CH3:28])=[N:21][C:22]([CH2:23][CH3:24])=[C:17]([C:16]2[CH:7]=[CH:8][C:9]3[CH2:10][CH2:11][CH2:12][CH2:13][C:14]=3[CH:15]=2)[N:18]=1)[CH3:32]
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

7

反応物 3

HCID 6228DimethylformamideHCID 12052TriethylsilaneHCID 222786903-{3,6-Diethyl-5-[(1-ethylpropyl)amino]pyrazin-2-yl}-5,6,7,8-tetrahydronaphthalen-2-yl trifluoromethanesulfonate

生成物 1

HCID 222787203,6-diethyl-N-(1-ethylpropyl)-5-(5,6,7,8-tetrahydronaphthalen-2-yl)pyrazin-2-amine収率 76%

試薬・触媒・溶媒 3

HCID 4366891
1,3-Bis(phenylphosphino)propane
触媒
HCID 962Water溶媒
HCID 8857Ethyl Acetate溶媒

反応条件

温度
60 °C

実験手順

A 7 mL oven dried vial was charged with 3-{3,6-diethyl-5-[(1-ethylpropyl)amino]pyrazin-2-yl}-5,6,7,8-tetrahydronaphthalen-2-yl trifluoromethanesulfonate (100 mg 0.2 mmol), 1,3-diphenylphosphinopropane (1.65 mg, 0.004 mmol), Pd(AcO)2 (0.9 mg, 0.004 mmol), and DMF (0.5 mL). The reaction was heated to 60° C. on the orbital shaker. Triethyl silane (0.08 mL, 0.5 mmol) was added at once. A color change from yellow to dark orange was observed. The vial was re-sealed with a teflon lined cap and heated to 60° C. for 2 hours. After cooling to ambient temperature, the reaction was diluted with ethyl acetate, poured in H2O, washed once with sat. aq. NaHCO3 and once with Brine. The organic layer was dried with Na2SO4, filtered and concentrated to 120 mg of a crude oil. The crude was purified by Biotage MPLC (40 g column, toluene) to give 53 mg (76%) of 3,6-diethyl-N-(1-ethylpropyl)-5-(5,6,7,8-tetrahydronaphthalen-2-yl)pyrazin-2-amine as a clear oil. Rf 0.18 (toluene). IR (liq.) 2964, 2933, 2874, 2858, 2837, 1558, 1508, 1483, 1463, 1444, 1392, 1381, 1212, 1173, 833 cm−1. OAMS supporting ions at: ESI+352.2. Anal. Calcd for C23H33N3: C, 78.58; H, 9.46; N, 11.95. Found: C, 78.20; H, 9.25; N, 11.95.

後処理

  1. customA 7 mL oven dried vial
  2. customlined cap
  3. temperatureheated to 60° C. for 2 hours
  4. temperatureAfter cooling to ambient temperature
  5. washwashed once with sat. aq. NaHCO3 and once with Brine
  6. dry with materialThe organic layer was dried with Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated to 120 mg of a crude oil
  9. customThe crude was purified by Biotage MPLC (40 g column, toluene)

出典と根拠

ORDレコード
ord-7517a9cb383744ddb7658176e4c76b06
出典データセット
uspto-grants-2005_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06964965B2

反応ノート

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