Diisopropylethylamine → Ethyl [4-({butyl[4-(4-chlorophenyl)pyrimidin-2-yl]amino}methyl)-2-methylphenoxy]acetate

HRID 1269628Notes

Reaction equation

[CH2:1]([NH:5][CH2:6][C:7]1[CH:19]=[CH:18][C:10]([O:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:9]([CH3:20])[CH:8]=1)[CH2:2][CH2:3][CH3:4].C(N(CC)C(C)C)(C)C.[Cl:30][C:31]1[CH:36]=[CH:35][C:34]([C:37]2[CH:42]=[CH:41][N:40]=[C:39](S(C)(=O)=O)[N:38]=2)=[CH:33][CH:32]=1>C(Cl)Cl>[CH2:1]([N:5]([CH2:6][C:7]1[CH:19]=[CH:18][C:10]([O:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:9]([CH3:20])[CH:8]=1)[C:39]1[N:38]=[C:37]([C:34]2[CH:35]=[CH:36][C:31]([Cl:30])=[CH:32][CH:33]=2)[CH:42]=[CH:41][N:40]=1)[CH2:2][CH2:3][CH3:4]

Participants

Conditions

Temperature: 100 °C

Procedure

To a mixture of the ethyl {4-[(butylamino)methyl]-2-methylphenoxy}acetate (686 mg, 2.46 mmol) and N,N-diisopropylethylamine (285 μL, 1.64 mmol) was added 4-(4-chlorophenyl)-2-(methylsulfonyl)pyrimidine (439 mg, 1.64 mmol) and the resultant mixture heated at 100° C. for 16 h in a reactivial. The cooled reaction mixture were then treated with N,N-diisopropylethylamine (285 μL, 1.64 mmol) and heated for a further 16 h at 100° C. in the reactivial. The cooled reaction mixtures were diluted with CH2Cl2 (30 mL), washed with water (20 mL), the aqueous extracted with CH2Cl2 (30 mL), the CH2Cl2 extracts combined and the solvent removed in vacuo. Purification by Biotage™ chromatography (silica, 90 g) eluted with 10:1 cyclohexane:EtOAc gave the title compound as a colourless gum (178 mg).

Workup

customThe cooled reaction mixture
customThe cooled reaction mixtures
washwashed with water (20 mL)
extractionthe aqueous extracted with CH2Cl2 (30 mL)
customthe solvent removed in vacuo
customPurification by Biotage™ chromatography (silica, 90 g)
washeluted with 10:1 cyclohexane

Sources & evidence

ORD record: ord-c68e20e8a43c4af8b660d33bd1a340f8
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07199239B2

Reaction notes

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