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2-Amino-4,6-dichloropyrimidine → 6-chloro-N4-(4-{[2-(trifluoromethyl)pyridin-4-yl]oxy}phenyl)pyrimidine-2,4-diamine

HRID 729924
ノート
印刷プレビュー

反応式

HRID 729924 の反応式
[NH2:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[C:4]([Cl:9])[N:3]=1.[F:10][C:11]([F:27])([F:26])[C:12]1[CH:17]=[C:16]([O:18][C:19]2[CH:24]=[CH:23][C:22]([NH2:25])=[CH:21][CH:20]=2)[CH:15]=[CH:14][N:13]=1>O.C(O)(C)C.Cl>[Cl:9][C:4]1[N:3]=[C:2]([NH2:1])[N:7]=[C:6]([NH:25][C:22]2[CH:23]=[CH:24][C:19]([O:18][C:16]3[CH:15]=[CH:14][N:13]=[C:12]([C:11]([F:27])([F:10])[F:26])[CH:17]=3)=[CH:20][CH:21]=2)[CH:5]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 2

HCID 655222-Amino-4,6-dichloropyrimidineHCID 591345604-{[2-(Trifluoromethyl)pyridin-4-yl]oxy}aniline2 回

生成物 1

HCID 578333536-chloro-N4-(4-{[2-(trifluoromethyl)pyridin-4-yl]oxy}phenyl)pyrimidine-2,4-diamine

試薬・触媒・溶媒 3

HCID 313Hydrochloric Acid溶媒HCID 962Water溶媒
HCID 3776
Isopropanol
溶媒

反応条件

温度
65 °C

実験手順

A stirred solution containing 2-amino-4,6-dichloropyrimidine (17.74 g, 0.11 mol) and 4-{[2-(trifluoromethyl)pyridin-4-yl]oxy}aniline (Intermediate 2U) in water (400 mL), isopropanol (100 mL) and concentrated hydrochloric acid (5 mL) was heated at 65° C. for 18 h. The reaction was cooled to 0° C. and the yellow-tan solid was collected by suction filtration and washed with water. The filtered product was dissolved in hot N,N-dimethylformamide (90° C.) and triethylamine was slowly added until the solution was slightly basic (pH˜8). The solution was then cooled to rt, added to vigorously stirred ice water (1.2 L), and stirring was continued for 1 h. The tan solids were collected by suction filtration and washed sequentially with water, isopropanol, diethyl ether and finally hexane. The material was dried by air suction to afford a light tan solid, 28.8 g (77%). 1H NMR (DMSO-d6) δ ppm 9.46 (s, 1H), 8.59 (d, 1H, J=5.6 Hz), 7.81 (d, 2H, J=9.0), 7.37 (d, 1H, J=2.4 Hz), 7.17 (d, 2H, J=9.0 Hz), 7.11 (dd, 1H, J=2.6, 5.6 Hz), 6.78 (s, 2H), 6.00 (s, 1H).

後処理

  1. temperatureThe reaction was cooled to 0° C.
  2. filtrationthe yellow-tan solid was collected by suction filtration
  3. washwashed with water
  4. dissolutionThe filtered product was dissolved in hot N,N-dimethylformamide (90° C.)
  5. additiontriethylamine was slowly added until the solution
  6. temperatureThe solution was then cooled to rt
  7. additionadded to vigorously stirred ice water (1.2 L)
  8. filtrationThe tan solids were collected by suction filtration
  9. washwashed sequentially with water, isopropanol, diethyl ether and finally hexane
  10. customThe material was dried by air suction
  11. customto afford a light tan solid, 28.8 g (77%)

出典と根拠

ORDレコード
ord-e12642cf67f341b38bd331d5685ed3a9
出典データセット
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07582645B2

反応ノート

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