Pyrrolidine → 2-(3,5-Dimethyl-4-(2-(pyrrolidin-1-yl)ethoxy)phenyl)-5,7-dimethoxypyrido[2,3-d]pyrimidin-4(3H)-one

HRID 591762Notes

Reaction equation

HRID 591762 reaction equation
Br[CH2:2][CH2:3][O:4][C:5]1[C:10]([CH3:11])=[CH:9][C:8]([C:12]2[NH:13][C:14](=[O:26])[C:15]3[C:21]([O:22][CH3:23])=[CH:20][C:19]([O:24][CH3:25])=[N:18][C:16]=3[N:17]=2)=[CH:7][C:6]=1[CH3:27].[NH:28]1[CH2:32][CH2:31][CH2:30][CH2:29]1>>[CH3:27][C:6]1[CH:7]=[C:8]([C:12]2[NH:13][C:14](=[O:26])[C:15]3[C:21]([O:22][CH3:23])=[CH:20][C:19]([O:24][CH3:25])=[N:18][C:16]=3[N:17]=2)[CH:9]=[C:10]([CH3:11])[C:5]=1[O:4][CH2:3][CH2:2][N:28]1[CH2:32][CH2:31][CH2:30][CH2:29]1

Participants

3

Reactant 2

HCID 31268PyrrolidineHCID 1363480292-[4-(2-bromo-ethoxy)-3,5-dimethyl-phenyl]-5,7-dimethoxy-3H-pyrido[2,3-d]pyrimidin-4-one

Product 1

HCID 1363480422-(3,5-Dimethyl-4-(2-(pyrrolidin-1-yl)ethoxy)phenyl)-5,7-dimethoxypyrido[2,3-d]pyrimidin-4(3H)-one

Procedure

A solution of 2-[4-(2-bromo-ethoxy)-3,5-dimethyl-phenyl]-5,7-dimethoxy-3H-pyrido[2,3-d]pyrimidin-4-one (0.20 g, 0.46 mmol) in pyrrolidine (2 mL) was stirred at room temperature for 3 hours. The excess pyrrolidine was removed under reduced pressure, and the residue was purified by column chromatography (silica gel 230-400 mesh; eluting with 2% 2.0 M ammonia in methanol solution and dichloromethane) to give the title compound as a white solid. Yield: 0.17 g (87%). MP 228-230° C. 1H NMR (400 MHz, CDCl3): δ 10.06 (s, 1H), 7.83 (s, 2H), 6.22 (s, 1H), 4.12 (s, 3H), 4.00 (s, 3H), 3.95 (t, J=6.0 Hz, 2H), 2.93 (t, J=6.0 Hz, 2H), 2.64 (m, 4H), 2.37 (s, 6H), 1.80 (m, 4H). MS (ES+) m/z: 425.19 (M+1).

Workup

  1. customThe excess pyrrolidine was removed under reduced pressure
  2. customthe residue was purified by column chromatography (silica gel 230-400 mesh; eluting with 2% 2.0 M ammonia in methanol solution and dichloromethane)

Sources & evidence

ORD record
ord-14b6af9fdc5e4f4eaa808f6daedd961c
Source dataset
uspto-grants-2016_01
Patent number
US09238640B2

Reaction notes

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