Hydrochloric Acid → 4-[(2,3,4,6-Tetrahydro-3-methyl-1-(2-methylpropyl)-6-(1-naphthalenylmethyl)-2,4-dioxo-1H-pyrrolo[3,4-d]pyrimidin-5-yl)thio]butanoic acid

HRID 322823Notes

Reaction equation

HRID 322823 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[C:6]2=[C:9]([S:23][CH2:24][CH2:25][CH2:26][C:27]([O:29]C)=[O:28])[N:10]([CH2:12][C:13]3[C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[CH:16]=[CH:15][CH:14]=3)[CH:11]=[C:5]2[N:4]([CH2:31][CH:32]([CH3:34])[CH3:33])[C:3]1=[O:35].Cl>O1CCCC1.CO>[CH3:1][N:2]1[C:7](=[O:8])[C:6]2=[C:9]([S:23][CH2:24][CH2:25][CH2:26][C:27]([OH:29])=[O:28])[N:10]([CH2:12][C:13]3[C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[CH:16]=[CH:15][CH:14]=3)[CH:11]=[C:5]2[N:4]([CH2:31][CH:32]([CH3:33])[CH3:34])[C:3]1=[O:35]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 9913628Methyl 4-[(2,3,4,6-tetrahydro-3-methyl-1-(2-methylpropyl)-6-(1-naphthalenylmethyl)-2,4-dioxo-1h-pyrrolo[3,4-d]pyrimidin-5-yl)thio]butanoate2×

Product 1

HCID 154914634-[(2,3,4,6-Tetrahydro-3-methyl-1-(2-methylpropyl)-6-(1-naphthalenylmethyl)-2,4-dioxo-1H-pyrrolo[3,4-d]pyrimidin-5-yl)thio]butanoic acid

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

The compound of Example 2, methyl 4-[(2,3,4,6-Tetrahydro-3-methyl-1-(2-methylpropyl)-6-(1-naphthalenylmethyl)-2,4dioxo-1H-pyrrolo[3,4-d]-pyrimidin-5-yl)thio]butanoate (400 mg), was dissolved in 3:1:1 tetrahydrofuran/methanol/1M lithium hydroxide and stirred for 1.5 h before being acidified by dropwise addition of concentrated hydrochloric acid (HCl). The mixture was then extracted with ethyl acetate. The organic phase was washed with brine, dried over magnesium sulphate (MgSO4) and evaporated to dryness in vacuo. The resultant yellow oil was chromatographed (silica), eluting with 200:10:1 dichloromethane/methanol/glacial acetic acid. The resultant red oil was dissolved in toluene and then evaporated, then similarly with trichloromethane to yield a pink foam. The foam was recrystallised from ethyl acetate/hexane to yield 129 mg of the title compound.

Workup

  1. extractionThe mixture was then extracted with ethyl acetate
  2. washThe organic phase was washed with brine
  3. dry with materialdried over magnesium sulphate (MgSO4)
  4. customevaporated to dryness in vacuo
  5. customThe resultant yellow oil was chromatographed (silica)
  6. washeluting with 200:10:1 dichloromethane/methanol/glacial acetic acid
  7. dissolutionThe resultant red oil was dissolved in toluene
  8. customevaporated
  9. customsimilarly with trichloromethane to yield a pink foam
  10. customThe foam was recrystallised from ethyl acetate/hexane

Sources & evidence

ORD record
ord-4c26ab6e856345a98779ec3111e59d66
Source dataset
uspto-grants-2001_04
Patent number
US06211368B1

Reaction notes

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