Sodium Hydroxide → HCID 22386534, compound

HRID 1072414Notes

Reaction equation

HRID 1072414 reaction equation
Cl[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:16]=[C:15]([S:17][CH2:18][CH3:19])[N:14]3[CH:20]=[CH:21][N:22]=[C:13]3[CH:12]=2)=[CH:7][C:6]=1[O:23][CH3:24].[OH-:25].[Na+]>N1CCOCC1>[CH2:18]([S:17][C:15]1[N:14]2[CH:20]=[CH:21][N:22]=[C:13]2[CH:12]=[C:11]([C:8]2[CH:9]=[CH:10][C:5]([O:4][CH2:3][CH2:2][N:14]3[CH2:20][CH2:21][O:25][CH2:12][CH2:13]3)=[C:6]([O:23][CH3:24])[CH:7]=2)[N:16]=1)[CH3:19]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22386539HCID 22386539, compound

Product 1

HCID 22386534HCID 22386534, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 8083MorpholineSolvent

Procedure

Then a solution of 7-[4-(2-Chloro-ethoxy)-3-methoxy-phenyl]-5-ethylsulfanyl-imidazo[1,2-c]pyrimidine (800 mg, 2.2 mmol) in morpholine (10 ml) was stirred at 100° C. overnight. After cooling to room temperature, the mixture was poured into a dilute NaOH solution and extracted with CH2Cl2. The combined organic extract was dried over MgSO4 and concentrated in vacuo. The crude product was purified by column chromatography to give 5-Ethylsulfanyl-7-[3-methoxy-4-(2-morpholin-4-yl-ethoxy)-phenyl]-imidazo[1,2-c]pyrimidine (650 mg, 71%).

Workup

  1. extractionextracted with CH2Cl2
  2. extractionThe combined organic extract
  3. dry with materialwas dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-0de37a3323ab4a19a6c6cf3a987c71d9
Source dataset
uspto-grants-2005_06
Patent number
US06911443B2

Reaction notes

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