Hydrochloric Acid → HCID 15300824, compound

HRID 863743Notes

Reaction equation

HRID 863743 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]2[CH2:7][O:8][C:9](=[O:10])[C:2]=12.[Li+].CC([N-]C(C)C)C.CS([C:23]1[N:28]=[C:27]([O:29][CH3:30])[CH:26]=[C:25]([O:31][CH3:32])[N:24]=1)(=O)=O.Cl>C1COCC1>[CH3:32][O:31][C:25]1[CH:26]=[C:27]([O:29][CH3:30])[N:28]=[C:23]([CH:7]2[C:3]3[C:2](=[N:1][CH:6]=[CH:5][CH:4]=3)[C:9](=[O:10])[O:8]2)[N:24]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8383634,6-Dimethoxy-2-(methylsulfonyl)pyrimidineHCID 2724682Lithium diisopropylamideHCID 12251968FURO[3,4-B]PYRIDIN-7(5H)-ONE

Product 1

HCID 15300824HCID 15300824, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1.3 g (0.0096 mols) of furo [3,4-b]pyridine-7(5H)-one in 50 ml of dry THF is cooled to -75° C. and 8 ml (0.0192 mols) of 2.5M LDA added dropwise over 5 minutes. The mixture is allowed to react for 1 hr at -750° C. and 2.1 g (0.0096 mol) of 2-methylsulfonyl-4,6-dimethoxypyrimidine in 30 ml of dry THF added dropwise over 10 minutes. The mixture is allowed to warm to RT, 1.6 ml of HCl added and the THF evaporated off. The residue is dissolved in 75 ml of CH2Cl2, washed with water (2×50 ml) and the organic phase concentrated to give a yellowish white gummy solid. This is chromatographed on a silica gel column using 50/50 hexane/ethyl acetate (500 ml), ethyl acetate (500 ml) and 80/20 acetone/methanol (1000 ml) (30 fractions). The crystalline residue (fractions 18-21) of the title product has m.p. of 167°-168° C.

Workup

  1. customto react for 1 hr at -750° C.
  2. customthe THF evaporated off
  3. dissolutionThe residue is dissolved in 75 ml of CH2Cl2
  4. washwashed with water (2×50 ml)
  5. concentrationthe organic phase concentrated
  6. customto give a yellowish white gummy solid
  7. customThis is chromatographed on a silica gel column

Sources & evidence

ORD record
ord-f09f1ac5d6af44b8939ba05133e56c4f
Source dataset
uspto-grants-1996_10
Patent number
US05561101

Reaction notes

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