N-methyl-2-pyrrolidone → HCID 86594941、化合物

HRID 969294

反応式

HRID 969294 の反応式
ClC1C(CCCl)=CN=C([NH:11][C:12]2[C:17]([CH3:18])=[CH:16][C:15]([CH3:19])=[CH:14][C:13]=2[CH3:20])N=1.[CH2:21]([CH:24]([NH2:28])[CH2:25][CH2:26][CH3:27])[CH2:22][CH3:23].[CH2:29]([CH:31]([NH2:35])[CH2:32][CH2:33][CH3:34])C.[CH3:36][N:37]1CCC[C:38]1=O>>[CH3:29][C:31]1[C:32]2[CH2:33][CH2:34][N:28]([CH:24]([CH2:25][CH2:26][CH3:27])[CH2:21][CH2:22][CH3:23])[C:36]=2[N:37]=[C:38]([C:15]2([CH3:19])[CH:14]=[C:13]([CH3:20])[C:12]([NH2:11])=[C:17]([CH3:18])[CH2:16]2)[N:35]=1

参加物

5

反応物 4

HCID 13387N-methyl-2-pyrrolidoneHCID 386654-HeptanamineHCID 86062Hexan-3-amineHCID 86594942HCID 86594942、化合物

生成物 1

HCID 86594941HCID 86594941、化合物収率 41%

反応条件

温度
120 °C

実験手順

A solution of [4-chloro-5-(2-chloro-ethyl)-pyrimidin-2-yl]-(2,4,6-trimethyl-phenyl)-amine (1.3 g, 4.1 mmol) in N-methylpyrrolidinone (15 mL) was treated with 1-propyl-butylamine (1.6 g, 14 mmol) and heated to 120° C. in a sealed tube for 18 hours. Additional 1-ethyl-butylamine (0.76 g, 6.6 mmol) was added, and heating at 120° C. was resumed for 32 hours. The reaction mixture was concentrated under reduced pressure and the resulting orange solid was partitioned between ethyl acetate (100 mL) and water (100 mL). The aqueous layer was further extracted with ethyl acetate (2×75 mL), and the combined extracts were washed with 15% aqueous sodium hydroxide (2×50 mL) and brine (30 mL), dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The crude brown oil was chromatographed over silica gel, eluting with a gradient of 1 to 15% methanol in dichloromethane, to provide VII as an off-white solid (0.64 g, 41%; ESIMS m/z (M+H)=367).

後処理

  1. temperatureheating at 120° C.
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe resulting orange solid was partitioned between ethyl acetate (100 mL) and water (100 mL)
  4. extractionThe aqueous layer was further extracted with ethyl acetate (2×75 mL)
  5. washthe combined extracts were washed with 15% aqueous sodium hydroxide (2×50 mL) and brine (30 mL)
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe crude brown oil was chromatographed over silica gel
  10. washeluting with a gradient of 1 to 15% methanol in dichloromethane

出典と根拠

ORDレコード
ord-893813ca57c548cca7e0ec165b7e0013
出典データセット
uspto-grants-2007_12
特許番号
US07307082B2

関連ノート

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