HCID 10701906, compound → HCID 178449216, compound

HRID 2371683Notes

Reaction equation

HRID 2371683 reaction equation
[C:1]([N:3]=[C:4](OCC)[CH2:5][CH2:6][CH3:7])#[N:2].[C:11]([C:13]1[CH:26]=[CH:25][C:16]2[O:17][C:18]([CH3:24])([CH3:23])[C@@H:19]([OH:22])[C@H:20]([NH2:21])[C:15]=2[CH:14]=1)#[N:12]>C(OCC)(=O)C>[C:11]([C:13]1[CH:26]=[CH:25][C:16]2[O:17][C:18]([CH3:24])([CH3:23])[C@@H:19]([OH:22])[C@H:20]([NH:21][C:4](=[N:3][C:1]#[N:2])[CH2:5][CH2:6][CH3:7])[C:15]=2[CH:14]=1)#[N:12]

Participants

4

Reactant 2

HCID 10701906HCID 10701906, compoundHCID 10943936(3S,4R)-4-amino-3-hydroxy-2,2-dimethyl-chroman-6-carbonitrile

Product 1

HCID 178449216HCID 178449216, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To 3.09 g of ethyl N-cyanobutyrimidate, 4.38 g of 6-cyano-3,4-dihydro-2,2-dimethyl-trans-4-amino-2H-benzo[b]pyran-3-ol was added, and the mixture was reacted under stirring at a temperature of from 100° to 120° C. for 2 hours. The reaction mixture was cooled, then dissolved in 100 ml of ethyl acetate, washed twice with a saturated sodium chloride aqueous solution and then dried over anhydrous sodium sulfate. Then, ethyl acetate was distilled off under reduced pressure. The residual oily substance was purified by silica gel column chromatography to obtain 3.54 g of the above identified compound in the form of crystals.

Workup

  1. customthe mixture was reacted
  2. temperatureThe reaction mixture was cooled
  3. washwashed twice with a saturated sodium chloride aqueous solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThen, ethyl acetate was distilled off under reduced pressure
  6. customThe residual oily substance was purified by silica gel column chromatography
  7. customto obtain 3.54 g of the

Sources & evidence

ORD record
ord-a74a41d8df2f49339aaadfc7d5ad6ae7
Source dataset
uspto-grants-1992_03
Patent number
US05095016

Reaction notes

Loading…