Sodium → HCID 57829865, compound

HRID 1855417Notes

Reaction equation

HRID 1855417 reaction equation
[Na].Cl[C:3]1[CH:8]=[C:7]([CH3:9])[N:6]=[C:5]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([N:17]3[CH:21]=[C:20]([CH3:22])[N:19]=[CH:18]3)=[C:13]([O:23][CH3:24])[CH:12]=2)[N:4]=1>CN(C)CCO>[CH3:18][N:17]([CH3:21])[CH2:14][CH2:13][O:23][C:3]1[CH:8]=[C:7]([CH3:9])[N:6]=[C:5]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([N:17]3[CH:21]=[C:20]([CH3:22])[N:19]=[CH:18]3)=[C:13]([O:23][CH3:24])[CH:12]=2)[N:4]=1

Participants

4

Reactant 2

HCID 5360545SodiumHCID 57829826HCID 57829826, compound

Product 1

HCID 57829865HCID 57829865, compoundYield 64.5%

Reagents, catalysts & solvents 1

HCID 79022-(Dimethylamino)ethanolSolvent

Conditions

Temperature
100 °C

Procedure

Sodium (10 mg, 0.45 mmol) was dissolved under an atmosphere of nitrogen in 2-dimethylaminoethanol (0.92 mL). (4-Chloro-6-methyl-pyrimidin-2-yl)-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-amine (99 mg, 0.3 mmol) was added and the suspension was heated to 100° C. for 2 hours. The solvent was evaporated under reduced pressure and the residue was taken up in water and extracted twice with diethyl ether. The combined organic layers were washed with brine, dried over sodium sulfate, filtered and evaporated under reduced pressure to dryness. The residue was purified by column chromatography on silica gel using dichloromethane/methanol/saturated aqueous ammonia solution (19:1:0.2 v/v/v) as eluent to yield the title compound as a brown viscous oil (37 mg, 33%). MS ISP (m/e): 383.2 (100) [(M+H)+]. 1H NMR (CDCl3, 300 MHz): δ (ppm)=7.74 (s, 1H), 7.62 (s, 1H), 7.15 (d, 1H), 7.07 (s, 1H), 7.05 (d, 1H), 6.87 (s, 1H), 6.16 (s, 1H), 4.45 (t, 2H), 3.86 (s, 3H), 2.71 (t, 2H), 2.36 (s, 3H), 2.34 (s, 6H), 2.30 (s, 3H).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. extractionextracted twice with diethyl ether
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure to dryness
  7. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-0fd4f779b04046c9828f521c3be4c24e
Source dataset
uspto-grants-2015_02
Patent number
US08962834B2

Reaction notes

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