Methyl iodide → 2-Amino-4-methylthio-6-(4-fluorophenyl)-pyrido(3,2-d)pyrimidine

HRID 1025521Notes

Reaction equation

HRID 1025521 reaction equation
[NH2:1][C:2]1[NH:3][C:4](=[S:19])[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.[OH-].[Na+].[CH3:22]I>C(OCC)C>[NH2:1][C:2]1[N:3]=[C:4]([S:19][CH3:22])[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

5

Reactant 3

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 178508162HCID 178508162, compound

Product 1

HCID 249572632-Amino-4-methylthio-6-(4-fluorophenyl)-pyrido(3,2-d)pyrimidineYield 72%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of the 2-amino-6-(4-fluorophenyl)-pyrido(3,2-d)pyrimidin-4(3H)thione of example 7 (55 mg) in a 1 N NaOH solution (10 ml) was added methyl iodide (0.2 mmol). The reaction was stirred at room temperature for 12 hours. The reaction mixture was diluted with diethyl ether and the organic layer was extracted with water. The combined organic layers were evaporated in vacuo and the crude residue was purified by preparative thin layer chromatography on silica, the mobile phase being a mixture of methanol and dichloromethane, in a volume ratio of 5:95, providing 41 mg of the pure title compound (yield: 72%) which was characterized by its mass spectrum as follows: MS (m/z): 287 ([M+H]+, 100).

Workup

  1. extractionthe organic layer was extracted with water
  2. customThe combined organic layers were evaporated in vacuo
  3. customthe crude residue was purified by preparative thin layer chromatography on silica
  4. additiona mixture of methanol and dichloromethane

Sources & evidence

ORD record
ord-d0344184b18d4bb89eabca7a200239bf
Source dataset
uspto-grants-2014_05
Patent number
US08729089B2

Reaction notes

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