Sodium Dithionite → HCID 57747399, compound

HRID 386623Notes

Reaction equation

HRID 386623 reaction equation
[O-]S(S([O-])=O)=O.[Na+].[Na+].[Br:9][C:10]1[CH:46]=[C:45]([CH3:47])[C:13]([O:14][C:15]2[C:20]([N+]([O-])=O)=[C:19](/[CH:24]=[CH:25]/[N:26](C)C)[N:18]=[C:17]([N:29]([C:37]3[CH:42]=[CH:41][C:40]([C:43]#[N:44])=[CH:39][CH:38]=3)[C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33])[N:16]=2)=[C:12]([CH3:48])[CH:11]=1>O.C1COCC1>[Br:9][C:10]1[CH:46]=[C:45]([CH3:47])[C:13]([O:14][C:15]2[C:20]3[NH:26][CH:25]=[CH:24][C:19]=3[N:18]=[C:17]([N:29]([C:37]3[CH:42]=[CH:41][C:40]([C:43]#[N:44])=[CH:39][CH:38]=3)[C:30](=[O:36])[O:31][C:32]([CH3:34])([CH3:33])[CH3:35])[N:16]=2)=[C:12]([CH3:48])[CH:11]=1

Participants

5

Reactant 2

HCID 24489Sodium DithioniteHCID 57747426HCID 57747426, compound

Product 1

HCID 57747399HCID 57747399, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of Na2S2O4 (40.04 g, 230 mmol) in water (100 ml) was added to a solution of (E)-tert-butyl 4-(4-bromo-2,6-dimethylphenoxy)-6-(2-(dimethylamino)vinyl)-5-nitropyrimidin-2-yl(4-cyanophenyl)carbamate (28.0 g, 45.9 mmol) in THF (300 ml). The mixture was stirred at room temperature of 2 days. The reaction mixture was concentrated. The residue was washed with water and extracted with ethyl acetate. The organic layer was concentrated and the product was obtained by crystallization from a mixture of water and methanol (18.15 g (mmol, 74%). 1H NMR (CDCl3, 400 MHz) δ 1.33 (s, 9H), 2.05 (s, 6H), 6.73 (d, J=3.8 Hz, 1H), 7.18 (d, J=8.8 Hz, 2H), 7.21 (s, 2H), 7.49 (d, J=8.8, 2H), 7.55 (d, J=3.8 Hz, 1H), 9.09 (s, 1H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. washThe residue was washed with water
  3. extractionextracted with ethyl acetate
  4. concentrationThe organic layer was concentrated
  5. customthe product was obtained by crystallization from a mixture of water and methanol (18.15 g (mmol, 74%)

Sources & evidence

ORD record
ord-076a07e4f5e6423e917301d80739401f
Source dataset
uspto-grants-2013_02
Patent number
US08372852B2

Reaction notes

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