2-Amino-5-pyrimidinemethanol

To a stirred solution of 2-aminopyrimidine-5-carbaldehyde (15, 500 mg, 4.06 mmol) in methanol (6 mL) was added sodium borohydride (200 mg, 5.28 mmol) in portions at 000. The resulting solution was slowly warmed to room temperature and was further stirred for 3 hours. After completion (monitored by TLC, 5percent MeOH in DCM, Rf 0.3), thereaction mixture was quenched by addition of saturated aqueous NH4CI solution and the resulting reaction mixture was concentrated under vacuo. The residue was directly loaded over a short column of silica gel (100-200 mesh) and eluted with gradient elution of 100percent DCM to 7.5percent MeOH in DCM. Concentration of fractions containing desired product afforded (2-aminopyrimidin-5-yl)methanol (16) as a light yellow solid. Yield: 340mg (67percent). 1H NMR (400 MHz, DMSO-d6) O 8.16 (5, 2H), 6.50 (brs, 2H), 4.99 (t, 1H), 4.26 (d, 2H). GCMS [mlz]: 125.0A solution of aldehyde (50 g, 0.41 mol) [see, for example, WO 0232893] in MeOH (300 mL) was cooled to 0° C. and carefully treated with NaBHA solution of aldehyde (50 g, 0.41 mol) [WO 0232893] in MeOH (300 mL) was cooled to 0 C and carefully treated with NaBH4 (20g, 0.53 mol in 6 batches) over 20 minutes. The reaction was then allowed to warm to 20 C and was stirred for 4 hours. The mixture was again cooled to 0 C, carefully quenched with saturated aqueous NH4CI, and concentrated. Flash chromatography (5- 10percent 7N NH3-MeOH/CH2CI2) provided the primary alcohol (31g, 62percent) as a light yellow solidStep 1: A solution of 68 (50 g, 0.41 mol) in CH30H (300 ml) was cooled to [0 °C] and carefully treated with NaBH4 (20g, 0.53 mol in 6 batches) over 20 min. The reaction was then allowed to warm to 20 [°C] and was stirred for 4 h. The mixture was again cooled to 0 [°C, ] carefully quenched with saturated aqueous [NH4CI, ] and concentrated. Flash chromatography (5-10percent 7N [NH3-CH3OH/CH2CI2)] provided 69 (31g, 62percent) as a light yellow solid.

Molecular Weight:125.13
XLogP3:-1
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:1
Exact Mass:125.058911855
Monoisotopic Mass:125.058911855
Topological Polar Surface Area:72
Heavy Atom Count:9
Complexity:80.3
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes