Diethyl Ether → HCID 57710300, compound

HRID 1038680Notes

Reaction equation

HRID 1038680 reaction equation
C[Mg]I.[CH2:4](OCC)C.[C:9]([C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19]2[N:24]=[CH:23][N:22]=[C:21]([N:25]([CH3:37])[C:26]([NH:28][C:29]3[C:34]([Cl:35])=[CH:33][CH:32]=[CH:31][C:30]=3[Cl:36])=[O:27])[CH:20]=2)=[CH:14][CH:13]=1)(=[O:11])[CH3:10]>C1COCC1>[Cl:35][C:34]1[CH:33]=[CH:32][CH:31]=[C:30]([Cl:36])[C:29]=1[NH:28][C:26](=[O:27])[N:25]([C:21]1[CH:20]=[C:19]([NH:18][C:15]2[CH:14]=[CH:13][C:12]([C:9]([OH:11])([CH3:4])[CH3:10])=[CH:17][CH:16]=2)[N:24]=[CH:23][N:22]=1)[CH3:37]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 57710307HCID 57710307, compoundHCID 178418373HCID 178418373, compound

Product 1

HCID 57710300HCID 57710300, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a freshly prepared solution of methylmagnesium iodide in diethyl ether (8 mL, ˜7 mmol) is added 1-[6-(4-acetyl-phenylamino)-pyrimidin-4-yl]-3-(2,6-dichloro-phenyl)-1-methyl-urea (0.5 g, 1.16 mmol) in several portions. After stirring for 5 h, THF (4 mL) is added. After 16 h the reaction is quenched by the addition of H2O and CH3OH and evaporated in vacuo. The residue is co-evaporated twice with toluene and purified by flash chromatography (CH2Cl2/CH3OH). The combined pure fractions are evaporated to afford the title compound.

Workup

  1. customAfter 16 h the reaction is quenched by the addition of H2O and CH3OH
  2. customevaporated in vacuo
  3. custompurified by flash chromatography (CH2Cl2/CH3OH)
  4. customThe combined pure fractions are evaporated

Sources & evidence

ORD record
ord-619321dd371e47118d8c07d172b5ef8a
Source dataset
uspto-grants-2013_10
Patent number
US08552002B2

Reaction notes

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