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Dimethylformamide → HCID 11749692、化合物

HRID 2216312
ノート
印刷プレビュー

反応式

HRID 2216312 の反応式
[CH3:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[C:14]([CH3:15])=[CH:13][C:12]([CH3:16])=[CH:11][C:10]=2[CH3:17])[C:5]([S:18]([C:21]2[CH:26]=[CH:25][C:24](OS(C(F)(F)F)(=O)=O)=[CH:23][CH:22]=2)(=[O:20])=[O:19])=[CH:4][N:3]=1.C([O-])(O)=O.[Na+].[CH3:40][N:41](C=O)C>[C-]#N.[Zn+2].[C-]#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[C:14]([CH3:15])=[CH:13][C:12]([CH3:16])=[CH:11][C:10]=2[CH3:17])[C:5]([S:18]([C:21]2[CH:26]=[CH:25][C:24]([C:40]#[N:41])=[CH:23][CH:22]=2)(=[O:20])=[O:19])=[CH:4][N:3]=1
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

6

反応物 3

HCID 6228DimethylformamideHCID 516892Sodium BicarbonateHCID 86595018HCID 86595018、化合物

生成物 1

HCID 11749692HCID 11749692、化合物収率 97%

試薬・触媒・溶媒 2

HCID 11186Zinc cyanide (Zn(CN)2)触媒
HCID 178418397
HCID 178418397、化合物
触媒

反応条件

温度
80 °C

実験手順

A mixture of trifluoromethanesulfonic acid 4-[2-methyl-4-(2,4,6-trimethylphenylamino)-pyrimidine-5-sulfonyl]-phenyl ester (146 mg, 0.283 mmol), zinc cyanide (66 mg, 0.57 mmol), and DMF (2 mL) was degassed with N2 for 10 min, and then Pd(PPh3)4 (16 mg, 0.014 mmol) was added. The mixture was stirred at 80° C. under N2 for 2 h and then cooled to room temperature. The reaction mixture was treated with saturated aqueous NaHCO3, and extracted (3×) with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by chromatography on silica gel (67:33 hexanes/EtOAc) to provide the target compound (108 mg, 97%) as a white solid: mp 258–260° C.; 1H NMR (500 MHz, CDCl3) δ 8.76 (s, 1H), 8.21 (br s, 1H), 8.08 (d, J=8.6 Hz, 2H), 7.84 (d, J=8.6 Hz, 2H), 6.92 (s, 2H), 2.40 (s, 3H), 2.31 (s, 3H), 2.00 (s, 6H); ESI MS m/z 393 [(M+H)+, calcd for C21H21N4O2S, 393.1].

後処理

  1. customwas degassed with N2 for 10 min
  2. temperaturecooled to room temperature
  3. extractionextracted (3×) with EtOAc
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by chromatography on silica gel (67:33 hexanes/EtOAc)

出典と根拠

ORDレコード
ord-069cf8aee69d4ce4b43db1ad2e107cda
出典データセット
uspto-grants-2006_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07112585B2

反応ノート

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