Water → N-methyl-4-[4-[(3S)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidin-2-yl]aniline

HRID 2353631

反応式

HRID 2353631 の反応式
Cl[C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][C@@H:9]2[CH3:14])[CH:5]=[C:4]([CH2:15][S:16]([CH3:19])(=[O:18])=[O:17])[N:3]=1.O.[CH3:21][NH:22][C:23]1[CH:28]=[CH:27][C:26](B2OC(C)(C)C(C)(C)O2)=[CH:25][CH:24]=1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.C(COC)OC.C(O)C>[CH3:21][NH:22][C:23]1[CH:28]=[CH:27][C:26]([C:2]2[N:7]=[C:6]([N:8]3[CH2:13][CH2:12][O:11][CH2:10][C@@H:9]3[CH3:14])[CH:5]=[C:4]([CH2:15][S:16]([CH3:19])(=[O:18])=[O:17])[N:3]=2)=[CH:25][CH:24]=1

参加物

8

反応物 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 11957892N-methyl-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 57547356HCID 57547356、化合物

生成物 1

HCID 59380133N-methyl-4-[4-[(3S)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidin-2-yl]aniline収率 90.2%

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 6228Dimethylformamide溶媒HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
90 °C

実験手順

2-Chloro-4-[(3S)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidine (1.01 g, 3.30 mmol) was dissolved in 18% DMF in 7:3:2 dimethoxy ethane:water:ethanol (7 mL). N-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (1.00 g, 4.29 mmol), 2M sodium carbonate solution (4 mL) and dichlorobis(triphenylphosphine) palladium (116 mg, 0.16 mmol) were added to the solution. The reaction was refluxed at 90° C. for 3 hours under nitrogen atmosphere then the mixture allowed to cool and partitioned ethyl acetate (30 mL) and water (30 mL). The organic layer was dried over magnesium sulphate, filtered and evaporated to dryness. The brown oil was dissolved in DCM and filtered to remove insoluble material then the filtrate chromatographed on silica, eluting with 0-4% methanol in DCM, to give the desired product as a yellow foam (1.12 g, 90%)

後処理

  1. temperatureto cool
  2. custompartitioned ethyl acetate (30 mL) and water (30 mL)
  3. dry with materialThe organic layer was dried over magnesium sulphate
  4. filtrationfiltered
  5. customevaporated to dryness
  6. dissolutionThe brown oil was dissolved in DCM
  7. filtrationfiltered
  8. customto remove insoluble material
  9. customthe filtrate chromatographed on silica
  10. washeluting with 0-4% methanol in DCM

出典と根拠

ORDレコード
ord-19fef6f66f7647aeb4f6d086802b9327
出典データセット
uspto-grants-2010_07
特許番号
US07750003B2

関連ノート

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