4,6-Dichloropyrimidine → HCID 86747306, compound

HRID 1656338Notes

Reaction equation

HRID 1656338 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:11][C:10]([CH3:13])([CH3:12])[C@@H:9]([OH:14])[C@H:8]([NH2:15])[C:7]=2[CH:16]=1)#[N:2].[Cl:17][C:18]1[CH:23]=[C:22](Cl)[N:21]=[CH:20][N:19]=1>C(O)C.C(N(CC)CC)C>[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:11][C:10]([CH3:13])([CH3:12])[C@@H:9]([OH:14])[C@H:8]([NH:15][C:22]3[CH:23]=[C:18]([Cl:17])[N:19]=[CH:20][N:21]=3)[C:7]=2[CH:16]=1)#[N:2]

Participants

5

Reactant 2

HCID 709434,6-DichloropyrimidineHCID 10943936(3S,4R)-4-amino-3-hydroxy-2,2-dimethyl-chroman-6-carbonitrile

Product 1

HCID 86747306HCID 86747306, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8471TriethylamineSolvent

Procedure

A solution of trans-6-cyano-4-amino-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-3-ol (prepared as described in U.S. Pat. No. 4,446,113) (2.0 g) and 4,6-dichloropyrimidine (1.5 g) in ethanol (25 mL) and triethylamine (1.3 mL) was heated under reflux for 72 h. The solution was allowed to cool and the precipitate filtered off, and dissolved in ethyl acetate. The ethyl acetate solution was washed with water, 0.5N hydrochloric acid, sodium bicarbonate solution, brine, and then dried (Na2SO4). Removal of drying agent and solvent gave the title compound as a solid (1.08 g). A sample recrystallised from acetonitrile had m.pt. 204°-8° C.

Workup

  1. temperatureunder reflux for 72 h
  2. temperatureto cool
  3. filtrationthe precipitate filtered off
  4. dissolutiondissolved in ethyl acetate
  5. washThe ethyl acetate solution was washed with water, 0.5N hydrochloric acid, sodium bicarbonate solution, brine
  6. dry with materialdried (Na2SO4)
  7. customRemoval
  8. customof drying agent and solvent

Sources & evidence

ORD record
ord-ccd342694f7e452084084d6ae1a1efc8
Source dataset
uspto-grants-1993_10
Patent number
US05254555

Reaction notes

Loading…