Citric Acid → Propane-1-sulfonic acid {6-[2-(5-methoxy-pyrimidin-2-yloxy)-ethoxy]-5-p-tolyl-pyrimidin-4-yl}-amide

HRID 2252726Notes

Reaction equation

HRID 2252726 reaction equation
[OH:1][CH2:2][CH2:3][O:4][C:5]1[N:10]=[CH:9][N:8]=[C:7]([NH:11][S:12]([CH2:15][CH2:16][CH3:17])(=[O:14])=[O:13])[C:6]=1[C:18]1[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=1.[H-].[Na+].CS([C:31]1[N:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][N:32]=1)(=O)=O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1>[CH3:38][O:37][C:34]1[CH:33]=[N:32][C:31]([O:1][CH2:2][CH2:3][O:4][C:5]2[N:10]=[CH:9][N:8]=[C:7]([NH:11][S:12]([CH2:15][CH2:16][CH3:17])(=[O:13])=[O:14])[C:6]=2[C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=2)=[N:36][CH:35]=1

Participants

6

Reactant 4

HCID 311Citric AcidHCID 24758Sodium hydrideHCID 41591512-methanesulfonyl-5-methoxypyrimidineHCID 86597591n-Propanesulfonic acid [6-(2-hydroxy-ethoxy)-5-p-tolyl-pyrimidin-4-yl]-amide

Product 1

HCID 59645267Propane-1-sulfonic acid {6-[2-(5-methoxy-pyrimidin-2-yloxy)-ethoxy]-5-p-tolyl-pyrimidin-4-yl}-amideYield 40.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

n-Propanesulfonic acid [6-(2-hydroxy-ethoxy)-5-p-tolyl-pyrimidin-4-yl]-amide (115.5 mg) was dissolved in THF (10 ml) and sodium hydride (60 mg) was added followed by stirring for 15 min at 50° C. Then 2-methanesulfonyl-5-methoxy-pyrimidine (138 mg) was added and stirring was continued for 8 h at 75° C. The reaction mixture was poured onto ice water, acidified with solid citric acid and extracted with ethyl acetate. The combined organic layers were dried over magnesium sulfate and the solvent was evaporated. The crude material was purified by plate chromatography with diethyl ether to give propane-1-sulfonic acid {6-[2-(5-methoxy-pyrimidin-2-yloxy)-ethoxy]-5-p-tolyl-pyrimidin-4-yl}-amide (61 mg) as a white powder. LC-MS: tR: 4.51, [M+H]+: 460.27.

Workup

  1. stirringstirring
  2. waitwas continued for 8 h at 75° C
  3. additionThe reaction mixture was poured onto ice water
  4. extractionextracted with ethyl acetate
  5. dry with materialThe combined organic layers were dried over magnesium sulfate
  6. customthe solvent was evaporated
  7. customThe crude material was purified by plate chromatography with diethyl ether

Sources & evidence

ORD record
ord-c9387b5c9d1d46d4bfd88d7ad5e573c6
Source dataset
uspto-grants-2008_01
Patent number
US07323465B2

Reaction notes

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