Chloromethyl Methyl Ether → HCID 68428546, compound

HRID 659961Notes

Reaction equation

HRID 659961 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:14]3=[N:15][CH:16]=[CH:17][CH:18]=[C:13]3[NH:12][C:11]=2[C:19]2[CH:24]=[CH:23][N:22]=[C:21]([S:25][CH3:26])[N:20]=2)=[CH:6][CH:5]=1.[CH3:27][O:28][CH2:29]Cl.[Cl-].[NH4+]>CN(C)C=O>[F:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[C:14]3=[N:15][CH:16]=[CH:17][CH:18]=[C:13]3[N:12]([CH2:27][O:28][CH3:29])[C:11]=2[C:19]2[CH:24]=[CH:23][N:22]=[C:21]([S:25][CH3:26])[N:20]=2)=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 68427420HCID 68427420, compound

Product 1

HCID 68428546HCID 68428546, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (130 mg, 2.8 mmoles 60% in oil) is added to a solution of 850 mg (2.53 mmoles) of 3-(4-Fluoro-phenyl)-2-(2-methylthio-pyrimidin-4-yl)-1H-pyrrolo[3,2-b]pyridine in 30 mL of dimethylformamide at room temperature. After 30 min. at room temperature, 0.23 mL of chloromethyl methyl ether is added to the reaction mixture. After 1 hour at room temperature, the reaction mixture is poured into ammonium chloride solution and extracted with ethyl acetate. The organic phase is washed with water and dried over magnesium sulfate. The solid residue is purified by chromatography on silica gel (ethyl acetate/hexane 2/1) to give 750 mg of 3-(4-Fluoro-phenyl)-1-methoxymethyl-2-(2-methylthio-pyrimidin-4-yl)-1H-pyrrolo[3,2-b]pyridine as white crystals.

Workup

  1. waitAfter 1 hour at room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic phase is washed with water
  4. dry with materialdried over magnesium sulfate
  5. customThe solid residue is purified by chromatography on silica gel (ethyl acetate/hexane 2/1)

Sources & evidence

ORD record
ord-055ad0610931433e937603656b455dcb
Source dataset
uspto-grants-2011_12
Patent number
US08084395B2

Reaction notes

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