Sodium Hydroxide → HCID 22258012, compound

HRID 567906Notes

Reaction equation

HRID 567906 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][CH:27]=[C:26]([N+:30]([O-])=O)[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]>[CH3:12][CH2:10][CH2:9][CH:6]([CH3:7])[CH3:5].[NH2:30][C:26]1[CH:25]=[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]([CH3:35])[CH3:36])[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:29]=[CH:28][CH:27]=1

Participants

8

Reactant 3

HCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 22258020HCID 22258020, compound

Product 2

HCID 78922-MethylpentaneHCID 22258012HCID 22258012, compoundYield 72.4%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A suspension of the partially purified 3-methyl-1-(2-methylpropyl)-6-(1-naphthalenylmethyl)-5-[(3-nitrophenyl)thio]thieno[2,3-d]pyrimidine-2,4-(1H, 3H)-dione (Example 30, 1.20 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 2 hours, then cooled to room temperature. 2M Sodium hydroxide solution (50 ml) was added and the mixture was stirred for 30 minutes. The resulting solution was decanted from insoluble solid. The solid and solution were in turn extracted with ethyl acetate (3×50 ml). The combined organic extracts were dried over anhydrous magnesium sulfate, filtered and evaporated under reduced pressure. The residue was purified by column chromatography over silica, eluting with ether:isohexane (2:1) followed by recrystallisation from ethyl acetate:isohexane to give the title compound (0.41 g).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 hours
  3. customThe resulting solution was decanted from insoluble solid
  4. extractionextracted with ethyl acetate (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 purified by column chromatography over silica
  9. washeluting with ether:isohexane (2:1)
  10. customfollowed by recrystallisation from ethyl acetate

Sources & evidence

ORD record
ord-3a57b6284cff4c30bf943f12903281d5
Source dataset
uspto-grants-2001_01
Patent number
US06180635B2

Reaction notes

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