Water → 4-[N-(2-Indanyl)-N-methylamino]-5-methylthieno[2,3-d]pyrimidine

HRID 48411Notes

Reaction equation

HRID 48411 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

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 99257354-(2-Indanylamino)-5-methylthieno[2,3-d]pyrimidine

Product 1

HCID 227196094-[N-(2-Indanyl)-N-methylamino]-5-methylthieno[2,3-d]pyrimidineYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A compound of the above Production Example 190, 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

  1. additionwas added
  2. stirringwas further stirred at room temperature for 30 minutes
  3. extractionwas extracted with chloroform
  4. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  5. customThe residue obtained
  6. distillationby distilling off the solvent under reduced pressure
  7. customwas purified by silica gel chromatography (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-2a64ca91d581426b9ef202748c3d931d
Source dataset
uspto-grants-2004_03
Patent number
US06703421B1

Reaction notes

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