Sodium Methoxide → HCID 59379912, compound

HRID 2353680Notes

Reaction equation

HRID 2353680 reaction equation
[CH3:1][C@H:2]1[CH2:7][O:6][CH2:5][CH2:4][N:3]1[C:8]1[CH:13]=[C:12]([CH2:14]OS(C)(=O)=O)[N:11]=[C:10]([C:20]2[CH:25]=[CH:24][C:23]([NH:26][C:27]([NH:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[O:28])=[CH:22][CH:21]=2)[N:9]=1.[CH3:36][O-:37].[Na+]>C(Cl)Cl.C(N(CC)CC)C>[CH3:36][O:37][CH2:14][C:12]1[CH:13]=[C:8]([N:3]2[CH2:4][CH2:5][O:6][CH2:7][C@@H:2]2[CH3:1])[N:9]=[C:10]([C:20]2[CH:21]=[CH:22][C:23]([NH:26][C:27]([NH:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[O:28])=[CH:24][CH:25]=2)[N:11]=1

Participants

5

Reactant 2

HCID 10942334Sodium MethoxideHCID 59380001HCID 59380001, compound

Product 1

HCID 59379912HCID 59379912, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

1-[4-[4-[(3S)-3-Methylmorpholin-4-yl]-6-(methylsulfonyloxymethyl)pyrimidin-2-yl]phenyl]-3-phenyl-urea (90 mg) dissolved in a solution of DCM (5 mL) and triethylamine (0.045 mL). Sodium methoxide (33% in methanol) (0.073 mL) was added to the reaction and the mixture stirred at RT for 18 h before being quenched with water and partitioned. The organic phase was dried over magnesium sulphate and evaporated to give a gum which was purified by prep-HPLC (basic) to give the desired compound (32 mg) as a white solid.

Workup

  1. custombefore being quenched with water
  2. custompartitioned
  3. dry with materialThe organic phase was dried over magnesium sulphate
  4. customevaporated
  5. customto give a gum which
  6. customwas purified by prep-HPLC (basic)

Sources & evidence

ORD record
ord-869dbd2ecf8e4b779fdb0a2fa484c4c8
Source dataset
uspto-grants-2010_07
Patent number
US07750003B2

Reaction notes

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