(R)-(2-chloro-6-(3-methylmorpholino)pyrimidin-4-yl)methanol synthesis
- Product Name:(R)-(2-chloro-6-(3-methylmorpholino)pyrimidin-4-yl)methanol
- CAS Number:1233339-70-2
- Molecular formula:C10H14ClN3O2
- Molecular Weight:243.69
1233339-69-9
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Yield:1233339-70-2 100%
Reaction Conditions:
Stage #1: methyl (R)-2-chloro-6-(3-methylmorpholino)pyrimidine-4-carboxylatewith lithium tetrahydridoborate in tetrahydrofuran at 0 - 20; for 18.8333 h;Inert atmosphere;
Stage #2: with water monomer in tetrahydrofuran;
Steps:
1.01.b
b) Lithium borohydride, 2M in THF (18 ml, 36.00 mmol) was added dropwise to (R)-methyl 2-chloro-6-(3-methylmorpholino)pyrimidine-4-carboxylate (16.28 g, 59.92 mmol) in THF (200 ml) at 0° C. over a period of 20 minutes under nitrogen. The resulting solution was stirred at 0° C. for 30 minutes and then allowed to warm to RT and stirred for a further 18 hours. Water (200 ml) was added and the THF evaporated. The aqueous layer was extracted with EtOAc (2×100 ml) and the organic phases combined, dried over MgSO4 and then evaporated to afford (R)-(2-chloro-6-(3-methylmorpholino)pyrimidin-4-yl)methanol (14.54 g, 100%) which was used in the next step without purification; 1H NMR (400 MHz, CDCl3) 1.32 (3H, d), 2.65 (1H, br s), 3.25-3.32 (1H, m), 3.51-3.57 (1H, m), 3.67-3.70 (1H, m), 3.78 (1H, d), 3.98-4.09 (2H, m), 4.32 (1H, br s), 4.59 (2H, s), 6.44 (1H, s); m/z: (ESI+) MH+, 244.40.
References:
US2011/306613,2011,A1 Location in patent:Page/Page column 21
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