Hydrochloric Acid → 2-chloro-5-fluoro-N-(3,4-ethylenedioxyphenyl)-4-pyrimidineamine

HRID 71277

反応式

HRID 71277 の反応式
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([F:9])=[CH:4][N:3]=1.N#N.[CH2:12]1[CH2:22][O:21][C:20]2[CH:19]=[CH:18][C:16]([NH2:17])=[CH:15][C:14]=2[O:13]1.Cl>O.CO>[Cl:1][C:2]1[N:7]=[C:6]([NH:17][C:16]2[CH:18]=[CH:19][C:20]3[O:21][CH2:22][CH2:12][O:13][C:14]=3[CH:15]=2)[C:5]([F:9])=[CH:4][N:3]=1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 947NitrogenHCID 891481,4-Benzodioxan-6-ylamineHCID 2507052,4-Dichloro-5-fluoropyrimidine2 回

生成物 1

HCID 220603622-chloro-5-fluoro-N-(3,4-ethylenedioxyphenyl)-4-pyrimidineamine収率 78%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒2 回

実験手順

The reaction flask equipped with a magnetic stifling bar and a rubber septum (to prevent loss of 2,4-dichloro-5-fluoropyrimidine and N2 inlet was charged with 3,4-ethylenedioxyaniline (34 g, 225 mmol), MeOH (100 mL), H2O (300 mL) and 2,4-dichloro-5-fluoropyrimidine (25 g, 150 mmol). The reaction mixture was stirred at room temperature for 1 h, diluted with H2O (1.5 liter), acidified with 2N HCl (200 mL) and sonicated. The solid obtained was filtered, washed with H2O and dried to obtain 33 g (78%) of the desired product, 2-chloro-N4-(3,4-ethylenedioxyphenyl)-5-fluoro-4-pyrimidineamine (R926087). 1H NMR (CDCl3): δ 8.02 (1H, d, J=3 Hz), 7.25 (d, 1H, J=1.2 Hz), 6.98 (dd, 1H, J=2.4 and 8.1 Hz), 6.85 (d, 1H, J=5.7 Hz), 4.27 (m, 4H); 19F NMR (CDCl3): −44570; LCMS: ret. time: 26.70 min.; purity 100%; MS (m/e): 283 (MH+).

後処理

  1. customThe reaction flask equipped with a magnetic stifling bar
  2. customsonicated
  3. customThe solid obtained
  4. filtrationwas filtered
  5. washwashed with H2O
  6. customdried

出典と根拠

ORDレコード
ord-581cee4e354d4d378891a0a75872ac95
出典データセット
uspto-grants-2014_09
特許番号
US08822685B2

関連ノート

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