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Water → N-butyl-N-ethyl-2,5-dimethyl-7-(2,4,6-trimethylphenyl)pyrrolo(2,3-d)pyrimidin-4-amine

HRID 1884344
ノート
印刷プレビュー

反応式

HRID 1884344 の反応式
Cl[C:2]1[C:3]2[C:11]([CH3:12])=[CH:10][N:9]([C:13]3[C:18]([CH3:19])=[CH:17][C:16]([CH3:20])=[CH:15][C:14]=3[CH3:21])[C:4]=2[N:5]=[C:6]([CH3:8])[N:7]=1.[CH2:22]([NH:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH3:23].O>CS(C)=O.Cl>[CH2:25]([N:24]([CH2:22][CH3:23])[C:2]1[C:3]2[C:11]([CH3:12])=[CH:10][N:9]([C:13]3[C:18]([CH3:19])=[CH:17][C:16]([CH3:20])=[CH:15][C:14]=3[CH3:21])[C:4]=2[N:5]=[C:6]([CH3:8])[N:7]=1)[CH2:26][CH2:27][CH3:28]
参加物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 962WaterHCID 25914ButylethylamineHCID 107805364-Chloro-7-mesityl-2,5-dimethyl-7H-pyrrolo[2,3-d]pyrimidine

生成物 1

HCID 5311055N-butyl-N-ethyl-2,5-dimethyl-7-(2,4,6-trimethylphenyl)pyrrolo(2,3-d)pyrimidin-4-amine収率 81.2%

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid触媒
HCID 679
Dimethyl Sulfoxide
溶媒

実験手順

A mixture of 4-chloro-2,5-dimethyl-7-(2,4,6-trimethylphenyl)-7H-pyrrolo[2,3-d]pyrimidine (1.000 g, 3.36 mmol) and N-ethylbutylamine (3.400 g, 33.60 mmol) in 5 ml of dimethylsulfoxide was heated to reflux for 1.5 hours. The mixture was cooled and treated with water and a few drops of 2 N HCl to pH 6.5 and extracted with ethyl acetate. The organic layer was separated, washed with dilute sodium bicarbonate, brine, and dried over sodium sulfate anhydrous and concentrated to dryness. The residue was purified through silica gel column chromatography to give 995 mg (81% yield) of the title compound as an oil. 1H NMR (CDCl3) δ 6 0.90 (t, 3H), 1.23(t, 3H), 1.35(m, 2H), 1.60-1.70(m, 2H), 1.92(s, 6H), 2.30(s, 3H), 2.40(s, 3H), 2.46(s, 3H), 3.58(t, 2H), 3.66(q, 2H), 6.55(s, 1H), 6.95(s, 2H) ppm. The corresponding hydrogen chloride salt was prepared as a white crystals after recrystallization from ethyl acetate. 1H NMR (D2O) δ 0.90(t, 3H), 1.34(m, 5H), 1.75(m, 2H), 1.90(s, 6H), 2.37(s, 3H), 2.48(s, 3H), 2.55(s, 3H), 3.80-3.94(m, 4H), 7.09(s, 2H) ppm.

後処理

  1. temperaturewas heated
  2. temperatureto reflux for 1.5 hours
  3. temperatureThe mixture was cooled
  4. extractionextracted with ethyl acetate
  5. customThe organic layer was separated
  6. washwashed with dilute sodium bicarbonate, brine
  7. dry with materialdried over sodium sulfate anhydrous
  8. concentrationconcentrated to dryness
  9. customThe residue was purified through silica gel column chromatography

出典と根拠

ORDレコード
ord-e6d9822e2f094164ac06e033b3a6fe2d
出典データセット
uspto-grants-2004_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06765008B1

反応ノート

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