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

HRID 2403562Notes

Reaction equation

HRID 2403562 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([O:8][C@H:9]([CH3:14])[C:10]([CH3:13])([OH:12])[CH3:11])[C:5]([I:15])=[CH:4][N:3]=1.[O:16]1[CH:21]=[CH:20][CH2:19][CH2:18][CH2:17]1.S(C1C=CC(C)=CC=1)([O-])(=O)=O.[NH+]1C=CC=CC=1>C(Cl)Cl>[Cl:1][C:2]1[N:7]=[C:6]([O:8][C@H:9]([CH3:14])[C:10]([CH3:11])([O:12][CH:17]2[CH2:18][CH2:19][CH2:20][CH2:21][O:16]2)[CH3:13])[C:5]([I:15])=[CH:4][N:3]=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

A solution of 4.96 g (14.5 mmol) of (R)-3-(2-chloro-5-iodopyrimidin-4-yloxy)-2-methylbutan-2-ol in 30 ml of DCM was admixed with 2.64 ml (29.0 mmol) of dihydropyrane and 0.36 g (1.5 mmol) of pyridinium tosylate and stirred for 22 hours at room temperature. The mixture was diluted with DCM and washed with saturated sodium hydrogen carbonate solution. The organic phase was dried (Na2SO4), filtered and concentrated by evaporation. The resulting residue was purified chromatographically (hexane/ethyl acetate 4:1). This gave 5.50 g (12.9 mmol; yield: 89%) of the diastereomer mixture.

Workup

  1. washwashed with saturated sodium hydrogen carbonate solution
  2. dry with materialThe organic phase was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated by evaporation
  5. customThe resulting residue was purified chromatographically (hexane/ethyl acetate 4:1)

Sources & evidence

ORD record
ord-024267b31d30452e9df1b17365cebd8e
Source dataset
uspto-grants-2014_08
Patent number
US08802686B2

Reaction notes

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