4-Chloro-6-hydrazinyl-2-methylpyrimidine → 4-chloro-6-(5-(3,4-dimethoxybenzyl)-1H-1,2,4-triazol-1-yl)-2-methylpyrimidine

HRID 1498799ノート

反応式

HRID 1498799 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][C:12](/[N:14]=[C:15](\N(C)C)/C)=O)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[Cl:20][C:21]1[CH:26]=[C:25]([NH:27][NH2:28])[N:24]=[C:23]([CH3:29])[N:22]=1>C(O)(=O)C>[Cl:20][C:21]1[CH:26]=[C:25]([N:27]2[C:12]([CH2:11][C:5]3[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=3)=[N:14][CH:15]=[N:28]2)[N:24]=[C:23]([CH3:29])[N:22]=1

参加物

4

反応物 2

HCID 135904704-Chloro-6-hydrazinyl-2-methylpyrimidineHCID 178490508HCID 178490508、化合物

生成物 1

HCID 715483344-chloro-6-(5-(3,4-dimethoxybenzyl)-1H-1,2,4-triazol-1-yl)-2-methylpyrimidine

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

A solution of (Z)-2-(3,4-dimethoxyphenyl)-N-(1-(dimethylamino)ethylidene)acetamide (1-2, 90 mg, 0.360 mmol, 1.0 eq) and 4-chloro-6-hydrazinyl-2-methylpyrimidine (57 mg, 0.360 mmol, 1.0 eq) in acetic acid (3 ml) was heated at 90° C. for 30 min. The reaction appeared complete by LCMS. The reaction mixture was concentrated and partitioned between dichloromethane (10 mL) and saturated aqueous sodium bicarbonate solution (10 mL). The organic layer was separated, dried over sodium sulfate, filtered and concentrated. The resulting residue was purified by silica gel column chromatography (0-100% ethyl acetate in hexanes) to afford 4-chloro-6-(5-(3,4-dimethoxybenzyl)-1H-1,2,4-triazol-1-yl)-2-methylpyrimidine (1-3). 1H NMR (500 MHz, CDCl3) δ 7.99 (s, 1H), 7.79 (s, 1H), 6.80 (m, 3H), 4.74 (s, 2H), 3.84 (s, 3H), 3.83 (s, 311), 2.76 (s, 3H). LRMS m/z (M+H) 346.4 found, 346.1 required

後処理

  1. concentrationThe reaction mixture was concentrated
  2. custompartitioned between dichloromethane (10 mL) and saturated aqueous sodium bicarbonate solution (10 mL)
  3. customThe organic layer was separated
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting residue was purified by silica gel column chromatography (0-100% ethyl acetate in hexanes)

出典と根拠

ORDレコード
ord-6e7e36bf909c46e2a7dd687934369179
出典データセット
uspto-grants-2015_12
特許番号
US09200001B2

反応ノート

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