2-Methoxyethanol → 2-Methyl-4-(2-methoxyethoxy)-6-(4-fluorophenyl)-pyrido[3,2-d]pyrimidine

HRID 1517451Notes

Reaction equation

HRID 1517451 reaction equation
[H-].[Na+].[CH3:3][C:4]1[N:5]=[C:6](Cl)[C:7]2[N:13]=[C:12]([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)[CH:11]=[CH:10][C:8]=2[N:9]=1.[CH3:22][O:23][CH2:24][CH2:25][OH:26]>>[CH3:3][C:4]1[N:5]=[C:6]([O:26][CH2:25][CH2:24][O:23][CH3:22])[C:7]2[N:13]=[C:12]([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)[CH:11]=[CH:10][C:8]=2[N:9]=1

Participants

4

Reactant 3

HCID 80192-MethoxyethanolHCID 24758Sodium hydrideHCID 576983684-Chloro-6-(4-fluorophenyl)-2-methylpyrido[3,2-d]pyrimidine

Product 1

HCID 576983182-Methyl-4-(2-methoxyethoxy)-6-(4-fluorophenyl)-pyrido[3,2-d]pyrimidineYield 88%

Procedure

Sodium hydride (80 mg of a 60% dispersion in mineral oil, 2.0 mmol) was added to 2-methoxyethanol (10 ml). The mixture was stirred at room temperature for 10 minutes. Then, 2-methyl-4-chloro-6-(4-fluorophenyl)-pyrido[3,2-d]pyrimidine (110 mg, 0.4 mmol) was added to this solution. The resulting mixture was stirred at room temperature for another 40 minutes. After concentration under reduced pressure, the residue was purified by silica gel flash chromatography, the mobile phase being a mixture of ethanol and dichloromethane, in a volume ratio of 1:100, affording the pure title compound (110 mg, yield 88%) as a white solid which was characterised as follows: MS (m/z): 314 ([M+H]+, 100).

Workup

  1. stirringThe resulting mixture was stirred at room temperature for another 40 minutes
  2. concentrationAfter concentration under reduced pressure
  3. customthe residue was purified by silica gel flash chromatography
  4. additiona mixture of ethanol and dichloromethane

Sources & evidence

ORD record
ord-6946c400dab54daeb1960fc577e7733b
Source dataset
uspto-grants-2012_07
Patent number
US08232278B2

Reaction notes

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