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

HRID 1498799노트

반응식

HRID 1498799 반응식
[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

참가 물질

4

반응물 2

HCID 135904704-Chloro-6-hydrazinyl-2-methylpyrimidineHCID 178490508HCID 178490508, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

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

후처리

  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)

출처 및 근거

ORD 기록
ord-6e7e36bf909c46e2a7dd687934369179
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09200001B2

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