3,4-dihydro-2H-pyran → HCID 118131366, compound

HRID 634423Notes

Reaction equation

HRID 634423 reaction equation
[I:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[N:8][C:9]=2[NH2:11])[NH:4][N:3]=1.[O:12]1[CH:17]=[CH:16][CH2:15][CH2:14][CH2:13]1.[OH2:18].[CH3:19][C:20]1C=C[C:23](S(O)(=O)=O)=[CH:22][CH:21]=1>CN(C=O)C>[I:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[N:8][C:9]=2[NH:11][CH:17]2[CH2:16][CH2:15][CH2:14][CH2:13][O:12]2)[N:4]([CH:23]2[CH2:22][CH2:21][CH2:20][CH2:19][O:18]2)[N:3]=1

Participants

5

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 521998p-Toluenesulfonic acid monohydrateHCID 178508725HCID 178508725, compound

Product 1

HCID 118131366HCID 118131366, compoundYield 77.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

to a solution of 3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine (1 g, 3.83 mmol) in dry DMF (15 mL), 3,4-dihydro-2H-Pyran (1.103 ml, 11.49 mmol) and 4-methylbenzenesulfonic acid monohydrate (0.208 ml, 0.958 mmol) were added. The solution was stirred for 5 days at 90° C. Solvent was removed and product was purified by Biotage Si 25 g with a gradient of heptane and ethyl acetate to give the title compound (320 mg, 19.5% yield).

Workup

  1. customSolvent was removed
  2. customproduct was purified by Biotage Si 25 g with a gradient of heptane and ethyl acetate

Sources & evidence

ORD record
ord-2888cb9afabc4573b545bf4715f0d4d7
Source dataset
uspto-grants-2016_04
Patent number
US09321776B2

Reaction notes

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