Ethanol → 4-Ethoxy-6-(4-fluorophenyl)pyrido[3,2-d]pyrimidin-2-amine

HRID 1025522Notes

Reaction equation

HRID 1025522 reaction equation
[NH2:1][C:2]1[N:3]=[C:4](SC)[C:5]2[N:11]=[C:10]([C:12]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=3)[CH:9]=[CH:8][C:6]=2[N:7]=1.[Na].[CH2:22]([OH:24])[CH3:23]>>[NH2:1][C:2]1[N:3]=[C:4]([O:24][CH2:22][CH3:23])[C:5]2[N:11]=[C:10]([C:12]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=3)[CH:9]=[CH:8][C:6]=2[N:7]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 5360545SodiumHCID 249572632-Amino-4-methylthio-6-(4-fluorophenyl)-pyrido(3,2-d)pyrimidine

Product 1

HCID 689211024-Ethoxy-6-(4-fluorophenyl)pyrido[3,2-d]pyrimidin-2-amineYield 72%

Procedure

To a solution of the 2-amino-4-methylthio-6-(4-fluorophenyl)-pyrido(3,2-d)pyrimidine of example 8 (700 mg) in ethanol (20 ml) was added 276 mg sodium. The reaction mixture was refluxed for 5 hours and then cooled down. The solvents were evaporated in vacuo and the crude residue was purified by silica gel flash chromatography, the mobile phase being a mixture of ethanol and dichloromethane, in a volume ratio gradually ranging from 3% to 5% ethanol, thus providing 490 mg of the pure title compound (72% yield), which was characterized by its mass spectrum as follows: MS (m/z): 285 ([M+H]+, 100).

Workup

  1. temperatureThe reaction mixture was refluxed for 5 hours
  2. temperaturecooled down
  3. customThe solvents were evaporated in vacuo
  4. customthe crude residue was purified by silica gel flash chromatography
  5. additiona mixture of ethanol and dichloromethane

Sources & evidence

ORD record
ord-91450939219f4c96991e3810a73a08c6
Source dataset
uspto-grants-2014_05
Patent number
US08729089B2

Reaction notes

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