HCID 11186195, compound → HCID 12097174, compound

HRID 1267031Notes

Reaction equation

[CH2:1]([Li])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[Cl:8][C:9]1[C:14]([C:15]2[C:20]([F:21])=[CH:19][C:18]([F:22])=[CH:17][C:16]=2[F:23])=[C:13](Cl)[N:12]2[N:25]=[CH:26][CH:27]=[C:11]2[N:10]=1>C1COCC1.[Cu](I)I>[Cl:8][C:9]1[C:14]([C:15]2[C:20]([F:21])=[CH:19][C:18]([F:22])=[CH:17][C:16]=2[F:23])=[C:13]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[N:12]2[N:25]=[CH:26][CH:27]=[C:11]2[N:10]=1

Participants

Conditions

Temperature: -70 °C

Procedure

Copper iodide (5 mmol) was suspended in THF (25 ml) under an inert gas atmosphere. The suspension was cooled to −70° C. and n-hexyllithium (5 ml,2M in hexanes) was added by syringe. The mixture was stirred for 45 minutes and 5,7-dichloro-6-(2,4,6-trifluorophenyl)-pyrazolo[1,5-α]pyrimidine (5 mmol, obtained from Example 3) was added as a solution in THF (10 min). The reaction mixture was stirred for 15 minutes at −70° C. The reaction mixture was then quenched with a mixture of aqueous saturated ammonium chloride/concentrated ammonia (9:1). The two phase mixture was separated. An oil was isolated from the organic layer which was subjected to chromatographic purification which yields the product as a crystalline residue.

Workup

stirringThe reaction mixture was stirred for 15 minutes at −70° C
customThe reaction mixture was then quenched with a mixture of aqueous saturated ammonium chloride/concentrated ammonia (9:1)
customThe two phase mixture was separated
customAn oil was isolated from the organic layer which
customwas subjected to chromatographic purification which
customyields the product as a crystalline residue

Sources & evidence

ORD record: ord-a46fef191bc642cc9aed03472d87027e
Source dataset: uspto-grants-2003_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06552026B2

Reaction notes

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