2-Amino-5-fluorophenol → Methyl 4-(4-fluoro-2-hydroxyphenylamino)-5-methylthieno[2,3-d]pyrimidine-6-carboxylate

HRID 532257Notes

Reaction equation

HRID 532257 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:14][C:8]2[N:9]=[CH:10][N:11]=[C:12](Cl)[C:7]=2[C:6]=1[CH3:15])=[O:4].[NH2:16][C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=1[OH:24].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>O1CCOCC1>[F:23][C:20]1[CH:21]=[CH:22][C:17]([NH:16][C:12]2[C:7]3[C:6]([CH3:15])=[C:5]([C:3]([O:2][CH3:1])=[O:4])[S:14][C:8]=3[N:9]=[CH:10][N:11]=2)=[C:18]([OH:24])[CH:19]=1

Participants

5

Reactant 3

HCID 1857632-Amino-5-fluorophenolHCID 521998p-Toluenesulfonic acid monohydrateHCID 2759834Methyl 4-chloro-5-methyl-thieno[2,3-d]pyrimidine-6-carboxylate

Product 1

HCID 58413076Methyl 4-(4-fluoro-2-hydroxyphenylamino)-5-methylthieno[2,3-d]pyrimidine-6-carboxylate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
140 °C

Procedure

4-Chloro-5-methyl-thieno[2,3-d]pyrimidine-6-carboxylic acid methyl ester (0.5 g), 2-amino-5-fluorophenol (265.0 mg), p-toluenesulfonic acid monohydrate (75.0 mg) and dioxane (5.0 ml) were combined in a microwave tube. The mixture was heated at 140° C. for 15 min under microwave irradiation. Then the mixture was allowed to cool to room temperature and a precipitate formed. The precipitate was collected by filtration, washed with dioxane, methanol and Et2O to yield the title compound.

Workup

  1. temperatureto cool to room temperature
  2. customa precipitate formed
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with dioxane, methanol and Et2O

Sources & evidence

ORD record
ord-f0706b0db6c148bc924368d0898e5959
Source dataset
uspto-grants-2014_10
Patent number
US08853193B2

Reaction notes

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