1-Methylimidazole → Diethyl 2-chloro-4-(4-chloro-5-(trifluoromethyl)pyrimidin-2-ylamino)-3-methoxybenzylphosphonate

HRID 2279863ノート

反応式

HRID 2279863 の反応式
Cl[C:2]1[N:7]=[C:6]([Cl:8])[C:5]([C:9]([F:12])([F:11])[F:10])=[CH:4][N:3]=1.[NH2:13][C:14]1[CH:28]=[CH:27][C:17]([CH2:18][P:19](=[O:26])([O:23][CH2:24][CH3:25])[O:20][CH2:21][CH3:22])=[C:16]([Cl:29])[C:15]=1[O:30][CH3:31].CN1C=CN=C1>[Cl-].[Cl-].[Zn+2].C(O)(C)(C)C.ClCCCl>[Cl:29][C:16]1[C:15]([O:30][CH3:31])=[C:14]([NH:13][C:2]2[N:7]=[C:6]([Cl:8])[C:5]([C:9]([F:12])([F:11])[F:10])=[CH:4][N:3]=2)[CH:28]=[CH:27][C:17]=1[CH2:18][P:19](=[O:26])([O:23][CH2:24][CH3:25])[O:20][CH2:21][CH3:22]

参加物

7

反応物 3

HCID 13901-MethylimidazoleHCID 27827742,4-Dichloro-5-(trifluoromethyl)pyrimidineHCID 86697801Diethyl 4-amino-2-chloro-3-methoxybenzylphosphonate

生成物 1

HCID 86697800Diethyl 2-chloro-4-(4-chloro-5-(trifluoromethyl)pyrimidin-2-ylamino)-3-methoxybenzylphosphonate

試薬・触媒・溶媒 3

HCID 3007855Zincchloride触媒HCID 111,2-Dichloroethane溶媒2 回HCID 6386tert-Butanol溶媒2 回

実験手順

To a solution of 2,4-dichloro-5-trifluoromethylpyrimidine (2.1 g, 9.77 mmol) in a 1:1 mixture of DCE and t-butanol (20 mL) was added ZnCl2 (1M, 10 mL) and stirred for half an hour at RT. After cooling at 0° C. diethyl 4-amino-2-chloro-3-methoxybenzylphosphonate (3 g, 9.77 mmol) in a 1:1 mixture of DCE and t-butanol (20 mL) was added followed by N-methylimidazole (800 mg, 9.75 mmol) drop wise while stirring was continued for 24 hrs. The solvents were removed under reduced pressure and the residue was purified by column chromatography (SiO2, ethyl acetate and hexanes (1:1)) to yield the desired compound in 1.5 g (32%) yield. 1H NMR (300 MHz, CDCl3) δ 8.61 (s, 1H), 8.38 (d, 1H), 8.03 (s, 1H), 4.01-4.18 (q, 4H), 3.98 (s, 3H), 3.29 (d, 2H), 1.24 (t, 6H).

後処理

  1. additionwas added
  2. stirringwhile stirring
  3. customThe solvents were removed under reduced pressure
  4. customthe residue was purified by column chromatography (SiO2, ethyl acetate and hexanes (1:1))

出典と根拠

ORDレコード
ord-f3ec5260c4db47e691feb64b374fb3d5
出典データセット
uspto-grants-2015_09
特許番号
US09133224B2

反応ノート

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