p-Toluenesulfonic acid → Methyl 4-(4-carbamoyl-2-ethoxyphenylamino)-5-methylthieno[2,3-d]pyrimidine-6-carboxylate

HRID 450528Notes

Reaction equation

HRID 450528 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][C:3]=1[O:11][CH2:12][CH3:13].Cl[C:15]1[C:16]2[C:23]([CH3:24])=[C:22]([C:25]([O:27][CH3:28])=[O:26])[S:21][C:17]=2[N:18]=[CH:19][N:20]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[OH-].[NH4+].O>O1CCOCC1>[C:6]([C:5]1[CH:9]=[CH:10][C:2]([NH:1][C:15]2[C:16]3[C:23]([CH3:24])=[C:22]([C:25]([O:27][CH3:28])=[O:26])[S:21][C:17]=3[N:18]=[CH:19][N:20]=2)=[C:3]([O:11][CH2:12][CH3:13])[CH:4]=1)(=[O:7])[NH2:8]

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 2759834Methyl 4-chloro-5-methyl-thieno[2,3-d]pyrimidine-6-carboxylateHCID 633567064-Amino-3-ethoxybenzamideHCID 86589665Water ammonium hydroxide

Product 1

HCID 46182171Methyl 4-(4-carbamoyl-2-ethoxyphenylamino)-5-methylthieno[2,3-d]pyrimidine-6-carboxylate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

4-amino-3-ethoxy-benzamide (0.045 g, 0.25 mmol), methyl 4-chloro-5-methyl-thieno[2,3-d]pyrimidine-6-carboxylate (0.061 g, 0.25 mmol, Fluorochem Ltd.) and para-toluene sulfonic acid (0.005 g, 0.025 mmol) were heated at reflux in anhydrous 1,4-dioxane (1.5 mL) for 16 hours. The solution was cooled to ambient temperature, ammonium hydroxide/water (1:4, 5 mL) added and the precipitate collected and washed successively with water and diethyl ether. The title compound was obtained as a yellow solid (0.057 g, 59%) after recrystallisation from MeOH.

Workup

  1. customthe precipitate collected
  2. washwashed successively with water and diethyl ether

Sources & evidence

ORD record
ord-2b315951797f4e8e90fd6e4c908ee0a7
Source dataset
uspto-grants-2013_07
Patent number
US08486953B2

Reaction notes

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