Sodium Hydroxide → HCID 22258014, compound

HRID 1611032Notes

Reaction equation

HRID 1611032 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[C:6]2[C:9]([S:23][C:24]3[CH:29]=[CH:28][C:27]([N+:30]([O-])=O)=[CH:26][CH:25]=3)=[C: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)[S:11][C:5]=2[N:4]([CH2:33][CH:34]([CH3:36])[CH3:35])[C:3]1=[O:37].[Cl-].[NH4+].[OH-].[Na+]>C(O)C.O.[Fe]>[NH2:30][C:27]1[CH:28]=[CH:29][C:24]([S:23][C:9]2[C:6]3[C:7](=[O:8])[N:2]([CH3:1])[C:3](=[O:37])[N:4]([CH2:33][CH:34]([CH3:36])[CH3:35])[C:5]=3[S:11][C:10]=2[CH2:12][C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=[CH:15][CH:14]=2)=[CH:25][CH:26]=1

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 22257984HCID 22257984, compound

Product 1

HCID 22258014HCID 22258014, compoundYield 5.5%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A suspension of the crude 3-methyl-1-(2-methylpropyl)-6-(1-naphthalenylmethyl)-5-[(4-nitrophenyl)thio]thieno[2,3-d]pyrimidine-2,4-(1H,3H)-dione (Example 35, 1.26 g), iron powder (0.59 g) and ammonium chloride (0.56 g) in ethanol (5 ml) and water (5 ml) was heated at reflux for 4 hours, then cooled to room temperature. Sodium hydroxide solution (10%, 50 ml) was added and the mixture was stirred for 1 hour. The resulting solution was decanted from insoluble solid. The solid and solution were in turn extracted with dichloromethane (3×50 ml) then ethyl acetate (3×50 ml). The combined organic extracts were dried over anhydrous magnesium sulfate, filtered and evaporated under reduced pressure. The residue was partially purified by column chromatography over silica, eluting with ethyl acetate:isohexane (1:1). Some pure material was recrystallised from isohexane:ethyl acetate to give the title compound (0.065 g). The remaining material was purified by preparative normal-phase HPLC with dichloromethane:ethanol gradient elution to give the title compound (0.163 g).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4 hours
  3. customThe resulting solution was decanted from insoluble solid
  4. extractionextracted with dichloromethane (3×50 ml)
  5. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customThe residue was partially purified by column chromatography over silica
  9. washeluting with ethyl acetate:isohexane (1:1)
  10. customSome pure material was recrystallised from isohexane

Sources & evidence

ORD record
ord-85aed90b4329450c9ee3befc90e83d46
Source dataset
uspto-grants-2006_01
Patent number
US06984644B2

Reaction notes

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