Acetic Acid → N-[[1-(2-chloro-5-phenyl-thieno[2,3-d]pyrimidin-4-yl)-4-piperidyl]methyl]-N,1-dimethyl-pyrrolidin-3-amine

Sodium triacetoxyborohydride (1.54 g, 7.28 mmol) was added to a stirred solution of 1-(2-chloro-5-phenyl-thieno[2,3-d]pyrimidin-4-yl)piperidine-4-carbaldehyde (1.3 g, 3.64 mmol), N,N′-dimethyl-3-aminopyrrolidine (519 ul, 4.00 mmol) and acetic acid (240 ul, 4.00 mmol) in dry dichloromethane (20 ml) at room temperature. The solution was stirred for ˜2 h, after which time the reaction had reached completion. Water (20 ml) was added and the organic layer separated, the aqueous phase was extracted with dichloromethane (×3) and the combined organics washed with brine, then dried (MgSO4) and evaporated. The crude residue was purified by flash column chromatography (0 to 5% 7.0M NH3/MeOH in dichloromethane). N—[[1-(2-chloro-5-phenyl-thieno[2,3-d]pyrimidin-4-yl)-4-piperidyl]methyl]-N,1-dimethyl-pyrrolidin-3-amine was isolated as a pale yellow oil (1.25 g, 76%). LCMS: (M+H)+ 456.2, RT=2.99.

1. customthe organic layer separated
2. extractionthe aqueous phase was extracted with dichloromethane (×3)
3. washthe combined organics washed with brine
4. dry with materialdried (MgSO4)
5. customevaporated
6. customThe crude residue was purified by flash column chromatography (0 to 5% 7.0M NH3/MeOH in dichloromethane)

ORD-Eintrag

ord-47f88e3f799d43e09444c5c091ea7533

Quelldatensatz

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09290511B2