Sodium Hydroxide → HCID 68462671, compound

HRID 502667Notes

Reaction equation

HRID 502667 reaction equation
[NH2:1][C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[C:9]([Br:17])[O:8][C:4]=2[N:5]=[CH:6][N:7]=1.C1(C)C(S(O[CH2:28][C@@H:29]2[CH2:33][CH2:32][CH2:31][O:30]2)(=O)=O)=CC=CC=1.[OH-].[Na+]>CN(C)C=O>[O:30]1[CH2:31][CH2:32][CH2:33][C@H:29]1[CH2:28][NH:1][C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[C:9]([Br:17])[O:8][C:4]=2[N:5]=[CH:6][N:7]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 58603291HCID 58603291, compoundHCID 86603228HCID 86603228, compound

Product 1

HCID 68462671HCID 68462671, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 4-amino-5-phenyl-6-bromofuro-[2,3-d]pyrimidine (0.99 g, 3.4 mmol) in dimethyl formamide (10 mL) was added 2-(S)-(toluenesulfonyloxymethyl)-tetrahydrofuran (0.88 g, 3.4 mmol) and sodium hydroxide powder (0.15 g, 3.8 mmol). The resulting mixture was stirred at 120° C. for 2 h. The mixture was then partitioned between ethyl acetate and water and the organic layer washed with brine, dried over magnesium sulfate and concentrated under reduced pressure. The crude solid was purified by flash column chromatography (10% ethyl acetate/hexane) to yield the product as a white solid (0.48 g, 38%).

Workup

  1. customThe mixture was then partitioned between ethyl acetate and water
  2. washthe organic layer washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe crude solid was purified by flash column chromatography (10% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-35f313e84afb49a0a087a7d0eb893cab
Source dataset
uspto-grants-2010_08
Patent number
US07776867B2

Reaction notes

Loading…