Acetic Acid → HCID 67491799, compound

HRID 1921146Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:4]=1[CH2:5][NH:6][CH:7]1[CH:12]2[CH2:13][CH2:14][N:9]([CH2:10][CH2:11]2)[CH:8]1[CH3:15].[Br:22][C:23]1[CH:24]=[N:25][C:26](Cl)=[N:27][CH:28]=1.C(O)(=O)C>O1CCOCC1>[Br:22][C:23]1[CH:24]=[N:25][C:26]([N:6]([CH2:5][C:4]2[CH:16]=[CH:17][C:18]([O:20][CH3:21])=[CH:19][C:3]=2[O:2][CH3:1])[CH:7]2[CH:12]3[CH2:13][CH2:14][N:9]([CH2:10][CH2:11]3)[CH:8]2[CH3:15])=[N:27][CH:28]=1

Participants

Conditions

Temperature: 150 °C

Procedure

(2,4-Dimethoxy-benzyl)-(2-methyl-1-aza-bicyclo[2.2.2]oct-3-yl)-amine (70 mg, 0.24 mmol) and 5-bromo chloropyrimidine (93 mg, 0.48 mmol) were dissolved in 1,4-dioxane (1 ml). Glacial acetic acid (42 □L, 0.72 mmol) was added and the reaction mixture was stirred under microwave radiation at 150° C. for 30 minutes. The reaction mixture was concentrated in vacuo, redissolved in EtOAc and washed with 1M aqueous sodium carbonate. The organic phase was dried (Na2SO4), filtered and concentrated in vacuo. The crude reaction mixture was purified by chromatography [eluent gradient: 10-30% MeOH/Et3N (9:1) in EtOAc) to give pure (5-bromo-pyrimidin-2-yl)-(2,4-dimethoxy-benzyl)-(2-methyl-1-aza-bicyclo[2.2.2]oct-3-yl)-amine.

Workup

concentrationThe reaction mixture was concentrated in vacuo
dissolutionredissolved in EtOAc
washwashed with 1M aqueous sodium carbonate
dry with materialThe organic phase was dried (Na2SO4)
filtrationfiltered
concentrationconcentrated in vacuo
customThe crude reaction mixture
customwas purified by chromatography [eluent gradient

Sources & evidence

ORD record: ord-02453bd63b874cc08cf8015dc169a01b
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08173667B2

Reaction notes

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