Water → 4-[N-(2-Indanyl)-N-methylamino]-5-methylthieno[2,3-d]pyrimidine
Reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[NH:10][C:11]1[C:12]2[C:19]([CH3:20])=[CH:18][S:17][C:13]=2[N:14]=[CH:15][N:16]=1.[H-].[Na+].[CH3:23]I.O>CN(C)C=O>[CH2:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH2:1][CH:2]1[N:10]([C:11]1[C:12]2[C:19]([CH3:20])=[CH:18][S:17][C:13]=2[N:14]=[CH:15][N:16]=1)[CH3:23]Participants
Procedure
A compound of the above Example 1, 4-(2-indanylamino)-5-methylthieno[2,3-d]pyrimidine (29 mg, 0.10 mmol), was dissolved in dry dimethylformamide (0.5 ml), to which sodium hydride (4.4 mg, 0.11 mmol) was added. After the mixture was stirred at room temperature for 10 minutes, methyl iodide (7.0 μl, 0.11 mmol) was added to the reaction mixture, which was further stirred at room temperature for 30 minutes. Water was added to the reaction mixture, which was extracted with chloroform, and the organic layer was dried over anhydrous sodium sulfate. The residue obtained by distilling off the solvent under reduced pressure was purified by silica gel chromatography (hexane:ethyl acetate=2:1) to obtain the title compound (20 mg, 0.070 mmol) having the following physical properties:
Workup
- additionwas added
- stirringwas further stirred at room temperature for 30 minutes
- extractionwas extracted with chloroform
- dry with materialthe organic layer was dried over anhydrous sodium sulfate
- customThe residue obtained
- distillationby distilling off the solvent under reduced pressure
- customwas purified by silica gel chromatography (hexane:ethyl acetate=2:1)
Sources & evidence
- ORD record
- ord-6cf30e5932de4d329ccdb03ff77543b6
- Source dataset
- uspto-grants-2004_05
- Patent number
- US06734180B1
Reaction notes
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