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

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Reaction Steps

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).

Provenance & Evidence