Ethyl Acetate → HCID 22258058, compound

HRID 1611044Notes

Reaction equation

HRID 1611044 reaction equation
[Cl-].[NH4+].[CH3:3][N:4]1[C:9](=[O:10])[C:8]2[C:11]([S:25][C:26]3[CH:31]=[CH:30][C:29]([N+:32]([O-])=O)=[CH:28][N:27]=3)=[C:12]([CH2:14][C:15]3[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[CH:18]=[CH:17][CH:16]=3)[S:13][C:7]=2[N:6]([CH2:35][CH:36]([CH3:38])[CH3:37])[C:5]1=[O:39].[OH-].[Na+].C(OCC)(=O)C>C(O)C.O.[Fe]>[NH2:32][C:29]1[CH:30]=[CH:31][C:26]([S:25][C:11]2[C:8]3[C:9](=[O:10])[N:4]([CH3:3])[C:5](=[O:39])[N:6]([CH2:35][CH:36]([CH3:38])[CH3:37])[C:7]=3[S:13][C:12]=2[CH2:14][C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]=[CH:17][CH:16]=2)=[N:27][CH:28]=1

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 22257966HCID 22257966, compound

Product 1

HCID 22258058HCID 22258058, compoundYield 56.1%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Iron powder (0.85 g) and ammonium chloride (0.81 g) were added to a stirred suspension of 3-methyl-1-(2-methylpropyl)-6-(1-naphthalenylmethyl)-5-[(5-nitropyridin-2-yl)thio]thieno[2,3-d]pyrimidine-2,4-(1H,3H)-dione (Example 37, 2.02 g) in ethanol (10 ml) and water (10 ml). The mixture was heated at reflux for 3 hours, then cooled to room temperature. 2M Sodium hydroxide solution (50 ml) was added and the mixture was stirred vigorously for 1 hour, ethyl acetate (100 ml) was added and the two-phase mixture was filtered. The solid and aqueous layer were in turn washed with ethyl acetate (100 ml). 2M Hydrochloric acid (25 ml) was added to the solid and the mixture was stirred for 1 hour, then added to the sodium hydroxide solution and extracted with ethyl acetate (2×100 ml). The combined organic extracts were dried over anhydrous magnesium sulfate, filtered and evaporated. The residue was recrystallised from ethyl acetate to give the title compound (1.07 g). The mother liquors were evaporated and purified by column chromatography over silica, eluting with ethyl acetate, and then recrystallised from ethyl acetate to give further title compound (0.665 g).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 3 hours
  3. filtrationthe two-phase mixture was filtered
  4. washwashed with ethyl acetate (100 ml)
  5. addition2M Hydrochloric acid (25 ml) was added to the solid
  6. stirringthe mixture was stirred for 1 hour
  7. additionadded to the sodium hydroxide solution
  8. extractionextracted with ethyl acetate (2×100 ml)
  9. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulfate
  10. filtrationfiltered
  11. customevaporated
  12. customThe residue was recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-16ab6f2644fd4e99a903e62e4ef3b14f
Source dataset
uspto-grants-2006_01
Patent number
US06984644B2

Reaction notes

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