Water → N4-(5-t-Butyl-isoxazol-3-yl)-N2-(4,5-dimethoxy-2-methyl-phenyl)-pyrimidine-2,4-diamine

HRID 1241591Notes

Reaction equation

[C:1]([C:5]1[O:9][N:8]=[C:7]([NH:10][C:11]2[CH:16]=[CH:15][N:14]=[C:13](Cl)[N:12]=2)[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:18][C:19]1[CH:25]=[C:24]([O:26][CH3:27])[C:23]([O:28][CH3:29])=[CH:22][C:20]=1[NH2:21].C([O-])(O)=O.[Na+].O>CS(C)=O.C(Cl)Cl>[C:1]([C:5]1[O:9][N:8]=[C:7]([NH:10][C:11]2[CH:16]=[CH:15][N:14]=[C:13]([NH:21][C:20]3[CH:22]=[C:23]([O:28][CH3:29])[C:24]([O:26][CH3:27])=[CH:25][C:19]=3[CH3:18])[N:12]=2)[CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 110 °C

Procedure

To a slurry of (5-L-butyl-isoxazol-3-yl)-(2-chloro-pyrimidin-4-yl)-amine (0.110 g, 0.435 mmol, Step A) in DMSO (0.110 mL) was added 2-methyl-4,5-dimethoxyaniline (0.073 g, 0.435 mmol). The mixture was heated in a sealed tube at 110° C. for 90 min until TLC indicated the disappearance of starting materials. The mixture was taken up in CH2Cl2 (5 mL) followed by the addition of NaHCO3 (aq., sat. 1 mL) and H2O (5 mL). Extraction with CH2Cl2 (5×5 mL), followed by drying with MgSO4 and filtration yielded a crude mixture that was concentrated under reduced pressure. Purification by chromatography (97:3 CH2Cl2:MeOH) on silica gel afforded the title compound as a purple solid. MS m/z=384.2. Calc'd for C20H25N5O3: 383.45.

Workup

extractionExtraction with CH2Cl2 (5×5 mL)
dry with materialby drying with MgSO4 and filtration
customyielded a crude mixture that
concentrationwas concentrated under reduced pressure
customPurification by chromatography (97:3 CH2Cl2:MeOH) on silica gel

Sources & evidence

ORD record: ord-d8183c2106594182a3c14c37a38e9539
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07115617B2

Reaction notes

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