M-Cresol → 2-[6-(3-Methylphenoxy)-pyrimidin-4-yl]amino-6-aminopyridine

HRID 2093497Notes

Reaction equation

Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([NH2:15])[N:10]=2)[CH:3]=1.[CH3:16][C:17]1[CH:18]=[C:19]([OH:23])[CH:20]=[CH:21][CH:22]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CCOC(C)=O>[CH3:16][C:17]1[CH:18]=[C:19]([CH:20]=[CH:21][CH:22]=1)[O:23][C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([NH2:15])[N:10]=2)[CH:3]=1

Participants

Conditions

Temperature: 145 °C

Procedure

To a solution of N2-(6-chloropyrimidin-4-yl)pyridine-2,6-diamine (100 mg, 0.45 mmol) in DMF (1 mL) was added 3-methylphenol (88 mg, 0.8 mmol) and anhydrous K2CO3 (93 mg, 0.6 mmol). The reaction mixture was heated at 145° C. for 16 h. It was then cooled and DMF was removed under reduced pressure to get a yellow gummy residue. The residue was taken in EtOAc (20 mL) and washed with water (5 mL), brine (5 mL) and dried over Na2SO4. Filtration followed by concentration under reduced pressure afforded a yellow gum which was further purified by column chromatography (SiO2, 60-120, EtOAc/hexane, 5/5) to give N2-(6-(3-methylphenoxy)pyrimidin-4-yl)pyridine-2,6-diamine (IR-12) (100 mg, 75%) as a pale yellow solid.

Workup

temperatureIt was then cooled
customDMF was removed under reduced pressure
customto get a yellow gummy residue
washwashed with water (5 mL), brine (5 mL)
dry with materialdried over Na2SO4
filtrationFiltration
concentrationfollowed by concentration under reduced pressure
customafforded a yellow gum which
customwas further purified by column chromatography (SiO2, 60-120, EtOAc/hexane, 5/5)

Sources & evidence

ORD record: ord-d00c3cce7b7b496abb142e2a26394844
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08445498B2

Reaction notes

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