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

HRID 1498799Notes

Reaction equation

HRID 1498799 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

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

Workup

  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)

Sources & evidence

ORD record
ord-6e7e36bf909c46e2a7dd687934369179
Source dataset
uspto-grants-2015_12
Patent number
US09200001B2

Reaction notes

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