Potassium Carbonate → 2-(6-aminopyridin-2-yl)propan-2-ol

HRID 1396462Notes

Reaction equation

Br[C:2]1[N:7]=[C:6]([C:8]([OH:11])([CH3:10])[CH3:9])[CH:5]=[CH:4][CH:3]=1.[OH-].[NH4+].C([O-])([O-])=O.[K+].[K+].C[N:21](C)CCN>[Cu-]=O.C(O)CO>[NH2:21][C:2]1[N:7]=[C:6]([C:8]([OH:11])([CH3:10])[CH3:9])[CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A heavy walled resealable tube was loaded under an argon atmosphere with copper (I) oxide (53.0 mg, 370 μmol), 2-(6-bromopyridin-2-yl)propan-2-ol (1600 mg, 7.4 mmol), ammonium hydroxide 28% solution (16.5 M) (8.98 mL, 148 mmol), K2CO3 (205 mg, 1.48 mmol), N,N-dimethylethylenediamine (65.3 mg, 81.3 μA, 740 μmol) and ethyleneglycol (14.8 mL). The reaction was stirred for 6 h at 60° C. After cooling to room temperature, the reaction mixture was extracted with dichloromethane (3×25 mL), combined organics dried over magnesium sulfate and evaporated. The residue was purified by flash chromatography (spherical silica 20-45 μM, 23 g, Versaflash Supelco) eluting with 0 to 5% over 20 min (10% ammonium hydroxide in methanol)/dichloromethane to give 2-(6-aminopyridin-2-yl)propan-2-ol (626 mg, 55.5% yield) as a light yellow liquid. 1H NMR (CHLOROFORM-d) δ: 7.44 (t, J=7.7 Hz, 1H), 6.67 (d, J=7.6 Hz, 1H), 6.38 (d, J=7.9 Hz, 1H), 5.12 (s, 1H), 4.38-4.55 (m, 2H), 1.49 (s, 6H); LC-MS 153.1, 155.1 [M+H]+.

Workup

temperatureAfter cooling to room temperature
extractionthe reaction mixture was extracted with dichloromethane (3×25 mL)
dry with materialcombined organics dried over magnesium sulfate
customevaporated
customThe residue was purified by flash chromatography (spherical silica 20-45 μM, 23 g, Versaflash Supelco)
washeluting with 0 to 5% over 20 min (10% ammonium hydroxide in methanol)/dichloromethane

Sources & evidence

ORD record: ord-64d4cfd5a32e451c9d29544b8ff0f317
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08901124B2

Reaction notes

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