Hydrochloric Acid → HCID 13912581, compound

HRID 1788696Notes

Reaction equation

HRID 1788696 reaction equation
[CH3:1][C:2]1[NH:3][CH:4]([O:31]C)[N:5]([S:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)(=[O:24])=[O:23])[CH:6]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-:21])=[O:20])[CH:14]=2)[C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9].Cl>O1CCCC1CO>[CH3:1][C:2]1[NH:3][C:4](=[O:31])[N:5]([S:22]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)(=[O:24])=[O:23])[CH:6]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-:21])=[O:20])[CH:14]=2)[C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86741697HCID 86741697, compound

Product 1

HCID 13912581HCID 13912581, compoundYield 40.8%

Reagents, catalysts & solvents 1

HCID 7360Tetrahydrofurfuryl alcoholSolvent

Procedure

A solution of 1, 2, 3, 6-tetrahydro-4-methyl-6-(3-nitrophenyl)-2-methoxy-1-(phenylsulfonyl)-5 -pyrimidinecarboxylic acid, ethyl ester (1.49 g, 3.24 mmol) in tetrahydrofuran-methanol (20 ml each) was treated with 5N hydrochloric acid (5.0 ml) and stirred at room temperature overnight. The reaction mixture was evaporated and partitioned between ethyl acetate and water. The organic phase was washed with saturated sodium bicarbonate and saturated sodium chloride. Flash chromatography (acetone/hexanes (1:5)) and crystallization from dichloromethane/isopropyl ether gave the title compound as white crystals (589 mg), melting point 187°-188° C. 3 Analysis Calc'd. for C20H19N3O7S: C, 53.93; H, 4.30; N, 9.43; S, 7.20. Found: C, 53.71; H, 4.19; N, 9.27; S, 7.13.

Workup

  1. customThe reaction mixture was evaporated
  2. custompartitioned between ethyl acetate and water
  3. washThe organic phase was washed with saturated sodium bicarbonate and saturated sodium chloride
  4. customFlash chromatography (acetone/hexanes (1:5)) and crystallization from dichloromethane/isopropyl ether

Sources & evidence

ORD record
ord-c8cc252a4d154990bb69632f1a9aae94
Source dataset
uspto-grants-1987_08
Patent number
US04684656

Reaction notes

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