Dimethylformamide → HCID 131724331, compound

HRID 2119781Notes

Reaction equation

HRID 2119781 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@@H:11]2[O:17][C@H:16]([C:18](=[SiH2:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[C@@:14]([C:25]([CH3:28])([CH3:27])[CH3:26])([OH:15])[C@H:12]2[OH:13])=[C:4]([NH2:29])[N:3]=1.[CH3:30]N(C=O)C.[H-].[Na+]>>[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@@H:11]2[O:17][C@H:16]([C:18](=[SiH2:24])[O:19][C:20]([CH3:22])([CH3:23])[CH3:21])[C@@:14]([C:25]([CH3:28])([CH3:27])[CH3:26])([OH:15])[C@H:12]2[O:13][CH3:30])=[C:4]([NH2:29])[N:3]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 131724332HCID 131724332, compound

Product 1

HCID 131724331HCID 131724331, compound

Conditions

Temperature
-20 °C

Procedure

To a stirred −20° C. solution of (62) (2.11 g, 5 mmol) in anhydrous DMF (40 ml) methyl iodide (0.93 ml, 15 mmol) was added followed by sodium hydride as a 60% mineral oil suspension (0.3 g, 7.5 mmol). The reaction mixture was stirred for 1.5 h at −20° C. and quenched with ammonium chloride (1.5 g). The resulting suspension was partitioned between chloroform (75 ml) and water (50 ml). The aqueous layer was washed with additional chloroform. The combined chloroform extracts were washed with 50 ml of water and the aqueous layer was extract back with chloroform. The resulting organic solution was dried over magnesium sulfate, filtered and the solvent was removed in vacuo. Crystallization from dichloromethane-hexane mixture (1:1) afforded (63) as colorless crystals. Yield 1.92 g (88%).

Workup

  1. customquenched with ammonium chloride (1.5 g)
  2. customThe resulting suspension was partitioned between chloroform (75 ml) and water (50 ml)
  3. washThe aqueous layer was washed with additional chloroform
  4. washThe combined chloroform extracts were washed with 50 ml of water
  5. extractionthe aqueous layer was extract back with chloroform
  6. dry with materialThe resulting organic solution was dried over magnesium sulfate
  7. filtrationfiltered
  8. customthe solvent was removed in vacuo
  9. customCrystallization from dichloromethane-hexane mixture (1:1)

Sources & evidence

ORD record
ord-6ef44f0002f0408fb402a672c4e7613b
Source dataset
uspto-grants-2004_02
Patent number
US06686463B2

Reaction notes

Loading…