Sodium Hydroxide → 5-(2,6-Difluorophenyl)aminomethyl-4-methylamino-2-methylthiopyrimidine

HRID 1858233ノート

反応式

HRID 1858233 の反応式
[CH3:1][NH:2][C:3]1[C:8]([CH:9]=S)=[CH:7][N:6]=[C:5](C)[N:4]=1.[F:12][C:13]1[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[C:14]=1[NH2:15].O.C1(C)C=C[C:25]([S:28](O)(=O)=O)=CC=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>C1(C)C=CC=CC=1.O.O1CCCC1>[F:12][C:13]1[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[C:14]=1[NH:15][CH2:9][C:8]1[C:3]([NH:2][CH3:1])=[N:4][C:5]([S:28][CH3:25])=[N:6][CH:7]=1

参加物

9

反応物 5

HCID 14798Sodium HydroxideHCID 796472,6-DifluoroanilineHCID 521998p-Toluenesulfonic acid monohydrateHCID 21226445Aluminium lithium hydrideHCID 865928692-Methyl-4-(methylamino)pyrimidine-5-carbothialdehyde

生成物 1

HCID 221251395-(2,6-Difluorophenyl)aminomethyl-4-methylamino-2-methylthiopyrimidine収率 236.2%

試薬・触媒・溶媒 3

HCID 962Water溶媒3 回HCID 1140Toluene溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of 300 mg (1.6 mmol) of 4-methylamino-2-methylthiopyrimidine-5-carboxaldehyde, 232 mg (1.8 mmol) of 2,6-difluoroaniline and 59 mg (0.3 mmol) of 4-toluenesulfonic acid monohydrate in 30 ml of toluene was heated at reflux with azeotropic removal of water for 18 hours. The mixture was cooled and evaporated. The residue was dissolved in 20 ml of tetrahydrofuran and added dropwise to a solution of 1.6 ml (1.6 mmol) of lithium aluminium hydride (1M in tetrahydrofuran) in a further 20 ml of tetrahydrofuran. After 30 minutes the mixture was cooled in ice and 0.5 ml of water, 0.75 ml of 2M sodium hydroxide solution and finally 1 ml of water were cautiously added dropwise. The resulting suspension was filtered through a filter aid and the filtrate was evaporated. The residue was subjected to column chromatography on silica gel using diethyl ether/hexane (1:1) for the elution to yield 210 mg (44%) of 5-(2,6-difluorophenyl)aminomethyl-4-methylamino-2-methylthiopyrimidine as a white solid. [Mass spectrum (ESI) MH+ =297].

後処理

  1. temperaturewas heated
  2. temperatureThe mixture was cooled
  3. customevaporated
  4. dissolutionThe residue was dissolved in 20 ml of tetrahydrofuran
  5. temperatureAfter 30 minutes the mixture was cooled in ice
  6. filtrationThe resulting suspension was filtered through a filter aid
  7. customthe filtrate was evaporated
  8. washfor the elution

出典と根拠

ORDレコード
ord-4a4a6f5f2aef4aff9b05b9cb0b9196ab
出典データセット
uspto-grants-2000_11
特許番号
US06150373

反応ノート

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