3,4-dihydro-2H-pyran → HCID 58467971, compound

HRID 1027854Notes

Reaction equation

HRID 1027854 reaction equation
[O:1]1[CH:6]=[CH:5][CH2:4][CH2:3][CH2:2]1.S(C1C=CC(C)=CC=1)([O-])(=O)=O.[NH+]1C=CC=CC=1.[Cl:24][C:25]1[N:30]=[C:29]([O:31][C@H:32]([CH3:37])[C:33]([CH3:36])([OH:35])[CH3:34])[C:28]([I:38])=[CH:27][N:26]=1>C(Cl)Cl>[Cl:24][C:25]1[N:30]=[C:29]([O:31][C@H:32]([CH3:37])[C:33]([CH3:34])([O:35][CH:6]2[CH2:5][CH2:4][CH2:3][CH2:2][O:1]2)[CH3:36])[C:28]([I:38])=[CH:27][N:26]=1

Participants

5

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 58467965HCID 58467965, compound

Product 1

HCID 58467971HCID 58467971, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2.64 ml (29.0 mmol) dihydropyran and 0.36 g (1.5 mmol) pyridinium tosylate were added to a solution of 4.96 g (14.5 mmol) (R)-3-(2-chloro-5-iodo-pyrimidin-4-yloxy)-2-methyl-butan-2-ol in 30 ml DCM and stirred for 22 hours at room temperature. The mixture was diluted with DCM and washed with saturated sodium hydrogencarbonate solution. The organic phase was dried (Na2SO4), filtered and concentrated by evaporation. The residue obtained was purified chromatographically (hexane/ethyl acetate 4:1). 5.50 g (12.9 mmol; yield: 89%) of the mixture of diastereomers was obtained.

Workup

  1. washwashed with saturated sodium hydrogencarbonate solution
  2. dry with materialThe organic phase was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated by evaporation
  5. customThe residue obtained
  6. customwas purified chromatographically (hexane/ethyl acetate 4:1)
  7. addition5.50 g (12.9 mmol; yield: 89%) of the mixture of diastereomers
  8. customwas obtained

Sources & evidence

ORD record
ord-8918f3f04cce4d3d9ea22fd312846cce
Source dataset
uspto-grants-2014_05
Patent number
US08735412B2

Reaction notes

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