(6-AMINO-3-PYRIDINYL)METHANOL

White to light yellow solid

Concentrated sulfuric acid (0.95 ml, 17.2 mmol, 0.5 equiv) is added to a solution of 6- aminonicotinic acid (5.0 g, 34.4 mmol) in ethanol (50 ml). After heating to reflux for 16 hours, the reaction mixture is carefully poured into a concentrated aqueous NaCompound 15 (1.0 equiv., 3.94 mmol, 0.600 g) was added portion wise to a suspension OfLiAlHTo a solution of acetic acid 6- (1, 3- dioxo-1, 3-dihydroisoindol-2-yl) pyridin-3-ylmethyl ester (0.200g, 0. 675mmol) was added methanol (lOmL). Hydrazine (0.065g, 2. 03mmol) was added and the mixture was heated to reflux for 2 hrs. A white precipitate formed after 30 min. The reaction was cooled to room temperature and filtered. The filtrate was concentrated and the residue was chromatographed on silica gel (Biotage 15, 15percent 7N methanol ammonium/dichloromethane) to give 0.025g (30percent) of the title compound as clear oil. LCMS (APCI+) RT=0. 31 min. m/z 125 (M+H) +.2-Aminopyridine-5-methanol, 262 (766 mg, 6.17 mmols) and butyraldehyde (445 mg, 6.17 mmmols) were dissolved in 45 ml of anhydrous 1, 2-dichloroethane and 20 ml of anhydrous MeCN. Sodium triacetoxyborohydride (1.31 g, 6.17 mmols) was added in one portion, followed by the addition of acetic acid (370 mg, 6.17 mmols). The mixture was stirred at room temperature 24 h. The mixture was diluted with 50 ml of EtOAc and then saturated solution of NaHC03 (60 ml) was added; the mixture was stirred 15 min. Phases were separated, the organic phase was dried over Na2S04, filtered and the solvent evaporated under vacuum. Crude yield, 0.80439 g (72% yield), was consistent with the title compound and was used as is without further purification. 1 H NMR (400 MHz, CDCl3) d 7.98 (d, 7 = 2.0 Hz, 1H), 7.47 (dd, 7 = 8.5, 2.4 Hz, 1H), 6.37 (d, 7 = 8.5 Hz, 1H), 4.53 (m, 3H), 3.24 (td, 7 = 7.1, 5.8 Hz, 2H), 1.64 - 1.54 (m, 2H), 1.42 (dq, 7 = 14.4, 7.3 Hz, 2H), 0.95 (t, 7 = 7.3 Hz, 3H). 13C NMR (101 MHz, CDCl3) d 158.85, 147.69, 137.82, 125.01, 106.38, 63.04, 42.21, 31.75, 20.32, 13.99.

Molecular Weight:124.14
XLogP3:-0.2
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:124.063662883
Monoisotopic Mass:124.063662883
Topological Polar Surface Area:59.1
Heavy Atom Count:9
Complexity:87.1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes