2-Methoxyethanol → HCID 57829761, compound

HRID 1855416Notes

Reaction equation

HRID 1855416 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.[CH3:25][O:26][CH2:27][CH2:28][OH:29]>>[CH3:25][O:26][CH2:27][CH2:28][O:29][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 3

HCID 80192-MethoxyethanolHCID 5360545SodiumHCID 57829826HCID 57829826, compound

Product 1

HCID 57829761HCID 57829761, compoundYield 37%

Conditions

Temperature
100 °C

Procedure

Sodium (10 mg, 0.45 mmol) was dissolved under an atmosphere of nitrogen in 2-methoxyethanol (0.95 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 (19:1 v/v) as eluent to yield the title compound as a yellow solid (41 mg, 37%). MS ISP (m/e): 370.2 (100) [(M+H)+]. 1H NMR (CDCl3, 300 MHz): δ (ppm)=7.74 (s, 1H), 7.63 (s, 1H), 7.18 (d, 1H), 7.05 (s, 1H), 7.03 (d, 1H), 6.87 (s, 1H), 6.18 (s, 1H), 4.51 (dd, 2H), 3.86 (s, 3H), 3.73 (dd, 2H), 3.45 (s, 3H), 2.35 (s, 3H), 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-bd3d4bf70d7c4c3a8ea811c68a7d9b31
Source dataset
uspto-grants-2015_02
Patent number
US08962834B2

Reaction notes

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