p-Toluenesulfonic acid monohydrate → Methyl 4-(4-fluoro-2-isopropoxyphenylamino)-5-methyl-thieno[2,3-d]pyrimidine-6-carboxylate
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].[F:16][C:17]1[CH:23]=[CH:22][C:20]([NH2:21])=[C:19]([O:24][CH:25]([CH3:27])[CH3:26])[CH:18]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>O1CCOCC1>[F:16][C:17]1[CH:23]=[CH:22][C:20]([NH:21][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:19]([O:24][CH:25]([CH3:27])[CH3:26])[CH:18]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 110 °C
Procedure
4-Chloro-5-methyl-thieno[2,3-d]pyrimidine-6-carboxylic acid methyl ester (112 mg), 4-fluoro-2-isopropoxyaniline (77.9 mg) and p-toluenesulfonic acid monohydrate (15 mg) were dissolved in dioxane (3.0 ml). The reaction was heated at 110° C. under microwave irradiation. Then the reaction mixture was concentrated in vacuo and the residue was dissolved in dichloromethane and extracted with water. The organic phase was dried and concentrated in vacuo. The residue was triturated with diisopropyl ether and filtered.
Workup
- concentrationThen the reaction mixture was concentrated in vacuo
- dissolutionthe residue was dissolved in dichloromethane
- extractionextracted with water
- customThe organic phase was dried
- concentrationconcentrated in vacuo
- customThe residue was triturated with diisopropyl ether
- filtrationfiltered
Sources & evidence
- ORD record
- ord-7a607f1f638641e6a9b8c8d92198a95a
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08853193B2
Reaction notes
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