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Hydrochloric Acid → 1-[6-(4,4-Dimethylcyclohexyl)-2-methylthieno[2,3-d]pyrimidin-4-yl]ethanone

HRID 2171794
Notes
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Reaction equation

HRID 2171794 reaction equation
ClC1C2C=C(C3CCC(C)(C)CC3)SC=2N=C(C)N=1.C([Sn](CCCC)(CCCC)C(OCC)=C)CCC.[NH4+].[Cl-].[CH3:40][C:41]1([CH3:62])[CH2:46][CH2:45][CH:44]([C:47]2[S:61][C:50]3[N:51]=[C:52]([CH3:60])[N:53]=[C:54]([C:55]([O:57]CC)=[CH2:56])[C:49]=3[CH:48]=2)[CH2:43][CH2:42]1.Cl>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCO.C1(C)C=CC=CC=1>[CH3:40][C:41]1([CH3:62])[CH2:46][CH2:45][CH:44]([C:47]2[S:61][C:50]3[N:51]=[C:52]([CH3:60])[N:53]=[C:54]([C:55](=[O:57])[CH3:56])[C:49]=3[CH:48]=2)[CH2:43][CH2:42]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 1180235544-Chloro-6-(4,4-dimethylcyclohexyl)-2-methylthieno[2,3-d]pyrimidineHCID 1180238626-(4,4-Dimethylcyclohexyl)-4-(1-ethoxyvinyl)-2-methylthieno[2,3-d]pyrimidine

Product 1

HCID 118023721
1-[6-(4,4-Dimethylcyclohexyl)-2-methylthieno[2,3-d]pyrimidin-4-yl]ethanone

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

To a mixture of 4-chloro-6-(4,4-dimethylcyclohexyl)-2-methylthieno[2,3-d]pyrimidine (1.0 g), tributyl(1-ethoxyvinyl)stannane (1.16 mL), and toluene (10.8 mL) was added Pd(PPh3)4 (392 mg), followed by heating to reflux for 5 hours. The reaction mixture was left to be cooled to room temperature, and to the reaction mixture were added a saturated aqueous NH4Cl solution, followed by extraction with EtOAc. The organic layer was washed sequentially with water and brine, dried over MgSO4, and then concentrated under reduced pressure to obtain a crude product (1.12 g) containing 6-(4,4-dimethylcyclohexyl)-4-(1-ethoxyvinyl)-2-methylthieno[2,3-d]pyrimidine. To this crude product were added EtOH (9.0 mL) and 1 M hydrochloric acid (10.2 mL) at room temperature, followed by stirring at 50° C. overnight. The reaction mixture was left to be cooled and concentrated under reduced pressure. To the residue was added water, followed by extraction with EtOAc. The organic layer was washed with brine, dried over MgSO4, and then concentrated under reduced pressure. The residue was purified by silica gel column to obtain 1-[6-(4,4-dimethylcyclohexyl)-2-methylthieno[2,3-d]pyrimidin-4-yl]ethanone (820 mg).

Workup

  1. temperatureby heating
  2. temperatureto reflux for 5 hours
  3. waitThe reaction mixture was left
  4. extractionfollowed by extraction with EtOAc
  5. washThe organic layer was washed sequentially with water and brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated under reduced pressure
  8. customto obtain a crude product (1.12 g)
  9. waitThe reaction mixture was left
  10. temperatureto be cooled
  11. concentrationconcentrated under reduced pressure
  12. additionTo the residue was added water
  13. extractionfollowed by extraction with EtOAc
  14. washThe organic layer was washed with brine
  15. dry with materialdried over MgSO4
  16. concentrationconcentrated under reduced pressure
  17. customThe residue was purified by silica gel column

Sources & evidence

ORD record
ord-6284229550a74002a720da9920457a6a
Source dataset
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09051339B2

Reaction notes

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