Methyl iodide → 5-(2-Amino-pyrimidin-4-yl)-1-methyl-1H-pyrrole-3-carboxylic acid ethyl ester

HRID 1619082Notes

Reaction equation

HRID 1619082 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][N:14]=[C:13]([NH2:17])[N:12]=2)[NH:8][CH:7]=1)=[O:5])[CH3:2].[H-].[Na+].[CH3:20]I>O1CCCC1.CS(C)=O>[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][N:14]=[C:13]([NH2:17])[N:12]=2)[N:8]([CH3:20])[CH:7]=1)=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 666782975-(2-Amino-pyrimidin-4-yl)-1H-pyrrole-3-carboxylic acid ethyl ester

Product 1

HCID 666784075-(2-Amino-pyrimidin-4-yl)-1-methyl-1H-pyrrole-3-carboxylic acid ethyl esterYield 82.3%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-(2-amino-pyrimidin-4-yl)-1H-pyrrole-3-carboxylic acid ethyl ester (5.1 g, 21.96 mmol) in tetrahydrofuran (70 mL) and dimethylsulfoxide (15 mL) cooled in a ice-water bath, NaH (0.96 g, 24.15 mmol) and methyl iodide (1.5 mL, 24.15 mmol) were added. The reaction was continued at room temperature for 12 h, tetrahydrofuran was removed under vacuo, then dichloromethane (200 mL) was added and the organic phase washed with water (100 mL). The aqueous fraction was extracted with dichloromethane (100 mL). The organic fractions were combined, dried over sodium sulfate, filtered, and concentered in vacuo. Purification by flash chromatography on silica gel (eluant: dichloromethane/ethanol 95/5) provided 4.45 g (82%) of the title compound as a pale yellow solid.

Workup

  1. customtetrahydrofuran was removed under vacuo
  2. additiondichloromethane (200 mL) was added
  3. washthe organic phase washed with water (100 mL)
  4. extractionThe aqueous fraction was extracted with dichloromethane (100 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customPurification by flash chromatography on silica gel (eluant: dichloromethane/ethanol 95/5)

Sources & evidence

ORD record
ord-55daa018dfc340c281ba199cf255b08f
Source dataset
uspto-grants-2014_07
Patent number
US08772280B2

Reaction notes

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