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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 1976831
Notes
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Reaction equation

HRID 1976831 reaction equation
C1(C)C=CC(S(=S)(OCCCC(OC)(OC)OC)=O)=CC=1.[CH3:22][N:23]1[C:28](=[O:29])[C:27]2=[C:30]([S:44][CH2:45][CH2:46][CH2:47][C:48]([O:50]C)=[O:49])[N:31]([CH2:33][C:34]3[C:43]4[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=4)[CH:37]=[CH:36][CH:35]=3)[CH:32]=[C:26]2[N:25]([CH2:52][CH:53]([CH3:55])[CH3:54])[C:24]1=[O:56].Cl>O1CCCC1.CO>[CH3:22][N:23]1[C:28](=[O:29])[C:27]2=[C:30]([S:44][CH2:45][CH2:46][CH2:47][C:48]([OH:50])=[O:49])[N:31]([CH2:33][C:34]3[C:43]4[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=4)[CH:37]=[CH:36][CH:35]=3)[CH:32]=[C:26]2[N:25]([CH2:52][CH:53]([CH3:54])[CH3:55])[C:24]1=[O:56]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

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]butanoateHCID 537006924,4,4-Trimethoxybutyl para-toluenethiosulphonate

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 acidYield 33.2%

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)-2,4-dioxo-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-164e52b52a9a477b88b493cde3a34255
Source dataset
uspto-grants-2001_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06229013B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes