Sodium bis(trimethylsilyl)amide → HCID 66611574, compound

HRID 1812400Notes

Reaction equation

HRID 1812400 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[C:8]([C:13]2[N:18]=[C:17]([CH3:19])[N:16]=[C:15]([NH2:20])[N:14]=2)[C:9](F)=[N:10][CH:11]=1)=[CH2:5])C.[C:21]1([S:27]([C:30]2[CH:31]=[C:32]([NH2:36])[CH:33]=[N:34][CH:35]=2)(=[O:29])=[O:28])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+]>C1COCC1.CCOC(C)=O>[NH2:20][C:15]1[N:16]=[C:17]([CH3:19])[N:18]=[C:13]([C:8]2[CH:7]=[C:6]([C:4](=[O:3])[CH3:5])[CH:11]=[N:10][C:9]=2[NH:36][C:32]2[CH:33]=[N:34][CH:35]=[C:30]([S:27]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)(=[O:29])=[O:28])[CH:31]=2)[N:14]=1

Participants

6

Reactant 3

HCID 2724254Sodium bis(trimethylsilyl)amideHCID 66599996HCID 66599996, compoundHCID 666118404-(5-(1-Ethoxyvinyl)-2-fluoropyridin-3-YL)-6-methyl-1,3,5-triazin-2-amine

Product 1

HCID 66611574HCID 66611574, compoundYield 44%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

4-(5-(1-Ethoxyvinyl)-2-fluoropyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine (255 mg, 0.925 mmol) and 5-(phenylsulfonyl)pyridin-3-amine (260 mg, 1.110 mmol) were dissolved in THF (9.2 mL) and the resulting mixture was cooled to 0° C. and NaHMDS in THF (1.0 M, Aldrich; 2775 μL, 2.77 mmol) was added. The reaction mixture was stirred at 0° C. for 1.5 h. The reaction mixture was then diluted with 100 mL of EtOAc, added to a separatory funnel, and partitioned with ammonium chloride (saturated, aqueous). The organic layer was separated, washed 2 times with 50 mL of ammonium chloride (saturated, aqueous), dried over sodium sulfate, and concentrated in vacuo. Chromatographic purification of the residue (silica gel, 0% to 3% (2 M ammonia in MeOH)/DCM) gave the title compound (44% yield) as a yellow amorphous solid. m/z (ESI, +ve ion) 462.2 (M+H)+.

Workup

  1. additionadded to a separatory funnel
  2. custompartitioned with ammonium chloride (saturated, aqueous)
  3. customThe organic layer was separated
  4. washwashed 2 times with 50 mL of ammonium chloride (saturated, aqueous)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customChromatographic purification of the residue (silica gel, 0% to 3% (2 M ammonia in MeOH)/DCM)

Sources & evidence

ORD record
ord-95b994105cd44392a4878b7e31c9edef
Source dataset
uspto-grants-2013_01
Patent number
US08362241B2

Reaction notes

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