1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 68982312, compound

HRID 2105303Notes

Reaction equation

HRID 2105303 reaction equation
C1CCN2C(=NCCC2)CC1.[Cl:12][C:13]1[CH:14]=[C:15]([NH:20][C:21]2[N:26]=[CH:25][N:24]=[C:23]([S:27][CH2:28]C(O)=O)[C:22]=2[C:32]#[N:33])[CH:16]=[CH:17][C:18]=1[F:19]>C1COCC1>[Cl:12][C:13]1[CH:14]=[C:15]([NH:20][C:21]2[C:22]3[C:32]([NH2:33])=[CH:28][S:27][C:23]=3[N:24]=[CH:25][N:26]=2)[CH:16]=[CH:17][C:18]=1[F:19]

Participants

4

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 68980434HCID 68980434, compound

Product 1

HCID 68982312HCID 68982312, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

DBU (0.88 mL, 5.9 mmol) was added to a solution of [6-(3-chloro-4-fluoro-phenylamino)-5-cyano-pyrimidin-4-ylsulfanyl]-acetic acid Compound 1h (2.0 g, 5.9 mmol) in THF (50 mL). The solution was heated to reflux for 24 hrs and then cooled to room temperature. The mixture was partitioned between EtOAc and 1 N NH4Cl. The organic layer washed twice with 1 N NH4Cl and once with brine. The organic solution was dried over Na2SO4, filtered and concentrated to dryness. The residue was purified by flash chromatography using gradient elution (20% EtOAc/80% Hexanes to 50% EtOAc/50% Hexanes) to yield N-(3-chloro-4-fluoro-phenyl)-thieno[2,3-d]pyrimidine-4,5-diamine Compound 84a (606 mg, 32%). MS 295 (M+H).

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux for 24 hrs
  3. customThe mixture was partitioned between EtOAc and 1 N NH4Cl
  4. washThe organic layer washed twice with 1 N NH4Cl and once with brine
  5. dry with materialThe organic solution was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness
  8. customThe residue was purified by flash chromatography
  9. washelution (20% EtOAc/80% Hexanes to 50% EtOAc/50% Hexanes)

Sources & evidence

ORD record
ord-87ad8a37620d4e34ba47452e02a75e56
Source dataset
uspto-grants-2009_08
Patent number
US07579356B2

Reaction notes

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