3,4-dihydro-2H-pyran → HCID 52945036, compound

HRID 2039461Notes

Reaction equation

HRID 2039461 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][CH:7]=[N:8]2)=[C:4](Cl)[N:3]=1.C(OCC)(=O)C.[O:18]1[CH:23]=[CH:22][CH2:21][CH2:20][CH2:19]1.[CH:24]1([NH2:27])[CH2:26][CH2:25]1>C(N(CC)CC)C>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH:23]2[CH2:22][CH2:21][CH2:20][CH2:19][O:18]2)=[C:4]([NH:27][CH:24]2[CH2:26][CH2:25]2)[N:3]=1

Participants

6

Reactant 4

HCID 80803,4-dihydro-2H-pyranHCID 8857Ethyl AcetateHCID 69828CyclopropylamineHCID 53244122,6-Dichloropurine

Product 1

HCID 52945036HCID 52945036, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

In a 3000 ml three-mouth bottle, 2,6-dichloropurine (300 g), ethyl acetate (1500 ml), pyridinium salt of paratoluenesulfonic acid (3 g) are mixed. The above mixture is stirred and heated to a temperature of 35° C., 2,3-dihydropyrane (360 ml) is added thereto within 30 min. The above mixture is reacted at 50˜60° C. for 5 h. The completion of reaction is checked with TCL analysis. Triethylamine (240 ml) is added to the bottle, and cyclopropylamine (204 ml) is added thereto under refluxing within 30 min. The above mixture is reacted at the temperature for 0.5 h. The completion of reaction is checked with TCL analysis. The reaction is cooled to room temperature. After filtration, a filter cake is completely washed with ethyl acetate, and a filtrate is washed with water for 3 times and delaminated. Organic layer is concentrated till large amount of solid is separated out. After filtration, a filter cake is washed with ethyl acetate for 3 times and then dried in vacuum at 50° C. for 5 h to obtain solid compound 2-choro-N-cyclopropyl-9-(tetrahydro-2H-pyran-2-yl)-9H-purine-6-amine (364 g).

Workup

  1. additionis added
  2. customThe above mixture is reacted at 50˜60° C. for 5 h
  3. customThe completion of reaction
  4. additionis added
  5. temperatureunder refluxing within 30 min
  6. customThe above mixture is reacted at the temperature for 0.5 h
  7. customThe completion of reaction
  8. filtrationAfter filtration
  9. washa filter cake is completely washed with ethyl acetate
  10. washa filtrate is washed with water for 3 times
  11. concentrationOrganic layer is concentrated till large amount of solid
  12. customis separated out
  13. filtrationAfter filtration
  14. washa filter cake is washed with ethyl acetate for 3 times
  15. customdried in vacuum at 50° C. for 5 h

Sources & evidence

ORD record
ord-f3e7952fe7f942d7942cf5b19e084170
Source dataset
uspto-grants-2013_11
Patent number
US08580763B2

Reaction notes

Loading…