Hydrochloric Acid → HCID 21109099, compound

HRID 1766100Notes

Reaction equation

HRID 1766100 reaction equation
[Sn](Cl)Cl.[NH2:4][C:5]1[C:13]2[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-])=O)[CH:15]=3)=[N:11][C:10]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[N:9][C:8]=2[S:7][C:6]=1[C:29]([O:31][CH2:32][CH3:33])=[O:30].Cl.[Na+].[Cl-]>O1CCOCC1.CCO>[NH2:4][C:5]1[C:13]2[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([NH2:20])[CH:15]=3)=[N:11][C:10]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[N:9][C:8]=2[S:7][C:6]=1[C:29]([O:31][CH2:32][CH3:33])=[O:30]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 24479Stannous ChlorideHCID 21109100HCID 21109100, compound

Product 1

HCID 21109099HCID 21109099, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

A solution of tin (II) chloride (23.0 g) in abs. EtOH (250 ml) was added to a solution of ethyl 5-amino-4-(3-nitrophenyl)-2-phenyl-thieno[2,3-d]pyrimidine-6-carboxylate (example 31(d), 16.6 g) in 1,4-dioxane p.a. (250 ml). 37% aq. HCl (6.9 ml) was added and the mixture was heated under reflux (90° C.) for 16 h. The mixture was allowed to cool to room temperature and concentrated under reduced pressure. The residue was suspended in EtOAc (500 ml). 4N aq. NaOH was added to obtain a pH of 10–11. The mixture was diluted by adding sat. aq. NaCl. The organic layer was separated, dried (MgSO4) and concentrated under reduced pressure.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto cool to room temperature
  3. concentrationconcentrated under reduced pressure
  4. addition4N aq. NaOH was added
  5. customto obtain a pH of 10–11
  6. additionThe mixture was diluted
  7. customThe organic layer was separated
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2fab1c63c1994f3291c22ba1e6f0247f
Source dataset
uspto-grants-2007_06
Patent number
US07229990B2

Reaction notes

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