Chloromethyl Methyl Ether → 3-(4-{2-[(3-Chloro-phenyl)-methoxymethyl-amino]-pyrimidin-4-yl}-pyridin-2-yl)-4-methyl-oxazolidin-2-one

HRID 1791135Notes

Reaction equation

HRID 1791135 reaction equation
CC(C)([O-])C.[K+].[Cl:7][C:8]1[CH:9]=[C:10]([NH:14][C:15]2[N:20]=[C:19]([C:21]3[CH:26]=[CH:25][N:24]=[C:23]([N:27]4[CH:31]([CH3:32])[CH2:30][O:29][C:28]4=[O:33])[CH:22]=3)[CH:18]=[CH:17][N:16]=2)[CH:11]=[CH:12][CH:13]=1.Cl[CH2:35][O:36][CH3:37]>C1COCC1>[Cl:7][C:8]1[CH:9]=[C:10]([N:14]([CH2:35][O:36][CH3:37])[C:15]2[N:20]=[C:19]([C:21]3[CH:26]=[CH:25][N:24]=[C:23]([N:27]4[CH:31]([CH3:32])[CH2:30][O:29][C:28]4=[O:33])[CH:22]=3)[CH:18]=[CH:17][N:16]=2)[CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 220278603-{4-[2-(3-Chloro-phenylamino)-pyrimidin-4-yl]-pyridin-2-yl}-4-methyl-oxazolidin-2-oneHCID 23665647Potassium tert-butoxide

Product 1

HCID 220278633-(4-{2-[(3-Chloro-phenyl)-methoxymethyl-amino]-pyrimidin-4-yl}-pyridin-2-yl)-4-methyl-oxazolidin-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Potassium t-butoxide (0.235 g, 2.1 mmol) is added at room temperature to a solution of 3-{4-[2-(3-chloro-phenylamino)-pyrimidin-4-yl]-pyridin-2-yl}-4-methyl-oxazolidin-2-one (0.5 g, 1.3 mmol). After stirring the mixture for 10 minutes chloromethylmethylether (0.17 g, 2.1 mmol) in THF (3 ml) is added. The mixture is stirred for additional 5 hours at this temperature. Dilution with ethyl acetate, washing with brine, drying over magnesium sulfate, filtering and evaporation of the solvent gives the title compound in form of a slightly colored oil; 1H-NMR (DMSO): 8.70 (s, 1H); 8.51 (d, 1H); 8.48 (d, 1H); 7.68 (d, 1H); 7.47–7.23 (m, 5H); 5.39 (s,2H); 4.87–4.74 (m,1H); 4.50 (dd, 1H); 4.08 (dd,1H); 3.25 (s,3H); 1.33 (d,3H).

Workup

  1. additionis added
  2. washDilution with ethyl acetate, washing with brine
  3. dry with materialdrying over magnesium sulfate
  4. filtrationfiltering
  5. customevaporation of the solvent

Sources & evidence

ORD record
ord-b25ff8a8ae9f4a798eef9fbbb9f0225d
Source dataset
uspto-grants-2006_07
Patent number
US07074787B2

Reaction notes

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