Cyclopropyl-(5-[(2,6-difluoro-3,5-dimethoxy-phenylimino)-methyl]-2-methylsulfanyl-pyrimidin-4-yl)-amine → Cyclopropyl-(5-[(2,6-difluoro-3,5-dimethoxy-phenylamino)-methyl]-2-methylsulfanyl-pyrimidin-4-yl)-amine

HRID 459955ノート

反応式

HRID 459955 の反応式
[CH:1]1([NH:4][C:5]2[C:10]([CH:11]=[N:12][C:13]3[C:18]([F:19])=[C:17]([O:20][CH3:21])[CH:16]=[C:15]([O:22][CH3:23])[C:14]=3[F:24])=[CH:9][N:8]=[C:7]([S:25][CH3:26])[N:6]=2)[CH2:3][CH2:2]1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH:1]1([NH:4][C:5]2[C:10]([CH2:11][NH:12][C:13]3[C:18]([F:19])=[C:17]([O:20][CH3:21])[CH:16]=[C:15]([O:22][CH3:23])[C:14]=3[F:24])=[CH:9][N:8]=[C:7]([S:25][CH3:26])[N:6]=2)[CH2:3][CH2:2]1

参加物

4

反応物 2

HCID 18444840Cyclopropyl-(5-[(2,6-difluoro-3,5-dimethoxy-phenylimino)-methyl]-2-methylsulfanyl-pyrimidin-4-yl)-amineHCID 21226445Aluminium lithium hydride

生成物 1

HCID 18444839Cyclopropyl-(5-[(2,6-difluoro-3,5-dimethoxy-phenylamino)-methyl]-2-methylsulfanyl-pyrimidin-4-yl)-amine収率 97%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A solution of in 8.61 g (22.6 mmol) of cyclopropyl-(5-[(2,6-difluoro-3,5-dimethoxy-phenylimino)-methyl]-2-methylsulfanyl-pyrimidin-4-yl)-amine in 400 mL of dry THF was cooled in an ice/water bath. To the cooled solution was added dropwise equivalent (22.6 mL, 22.6 mmol) of a 1 M LAH solution in THF. The reaction was stirred cold for 2 hours and then quenched by sequential addition of 0.4 mL water, followed by 1.6 mL of 15% NaOH solution, and finally 0.88 mL of water. The reaction was filtered through Celite and the filter pad was washed well with THF. The THF filtrate was concentrated in vacuo. The residue was dissolved in dichloromethane, washed with a saturated solution of NaCl, and concentrated in vacuo. Stirring the residue with diethyl ether and concentrating the suspension in vacuo gave 8.38 g (97%) of the title compound as a solid: mp 48° C.–50° C. MS (APCI) (m+1)/z 383.4 Analysis calculated for C17H20F2N4SO2: C, 53.39; H, 5.27; N, 14.65. Found: C, 53.44; H, 5.29; N, 14.31.

後処理

  1. customquenched by sequential addition of 0.4 mL water
  2. filtrationThe reaction was filtered through Celite
  3. washthe filter pad was washed well with THF
  4. concentrationThe THF filtrate was concentrated in vacuo
  5. dissolutionThe residue was dissolved in dichloromethane
  6. washwashed with a saturated solution of NaCl
  7. concentrationconcentrated in vacuo
  8. stirringStirring the residue with diethyl ether
  9. concentrationconcentrating the suspension in vacuo

出典と根拠

ORDレコード
ord-b185df528a5746fe9661f8f55ece2151
出典データセット
uspto-grants-2007_03
特許番号
US07196090B2

反応ノート

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