* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
With sodium tetrahydroborate; In methanol; at 0 - 20℃; for 3h;
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, 5% 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 100% DCM to 7.5% MeOH in DCM. Concentration of fractions containing desired product afforded (2-aminopyrimidin-5-yl)methanol (16) as a light yellow solid. Yield: 340mg (67%). 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]: 125.0
62%
With sodium tetrahydroborate; In methanol; at 0 - 20℃; for 4.33h;
A 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 NaBH4 (20 g, 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 NH4Cl, and concentrated. Flash chromatography (5-10% 7N NH3-MeOH/CH2Cl2) provided the primary alcohol (31 g, 62%) as a light yellow solid.
62%
With sodium tetrahydroborate; In methanol; at 0 - 20℃; for 260h;
A 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- 10% 7N NH3-MeOH/CH2CI2) provided the primary alcohol (31g, 62%) as a light yellow solid
62%
Step 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 (5-10% 7N [NH3-CH3OH/CH2CI2)] provided 69 (31g, 62%) as a light yellow solid.
With sodium tetrahydroborate; In methanol; water; N,N-dimethyl-formamide;
Example 85 (2-Amino-pyrimidin-5-yl)-methanol A solution of 2-Amino-pyrimidine-5-carbaldehyde (500 mg) in DMF:water:MeOH (4:1:1, 30 mL) was treated with NaBH4 (200 mg, excess) and stirred at RT for 30 minutes. The product could not be extracted into organics so the solvents were removed and the crude product was used directly in the subsequent reaction. MS 126 (M+H+).
Chemistry
Pharmaceutical Intermediates
Inhibitors/Agonists
Material Science
For Research Only
120K+ Compounds
Competitive Price
1-2 Day Shipping
