Methylamine → HCID 46784184, compound

Temperature

0 °C

Ti (OiPr)4 (1.3 eq) was added with stirring to MeNH2 (2.0 M in MeOH, 3 eq) under Ar. After 5 min. 5-methylthiazole-2-carbaldehyde (1 eq) was added, and the solution was stirred for 1-2 h. The reaction was cooled to 0° C. and NaBH4 (1.3 eq) was added. The solution was stirred at 0° C. to room temperature overnight. After quenching the reaction with water the mixture was filtered through Celite to remove the white ppt. MeOH was removed in vacuo and the residue was diluted with EtOAc. The resulting solution was washed with water (×3), brine (×1), and dried over Na2SO4. The inorganic material was filtered off, and the solvent was removed in vacuo to give the crude product. Purification via column chromatography yielded N-methyl-1-(5-methylthiazol-2-yl)methanamine in 80-85% yield.

1. stirringThe solution was stirred at 0° C. to room temperature overnight
2. customAfter quenching
3. customthe reaction with water the mixture
4. filtrationwas filtered through Celite
5. customto remove the white ppt
6. customMeOH was removed in vacuo
7. additionthe residue was diluted with EtOAc
8. washThe resulting solution was washed with water (×3), brine (×1)
9. dry with materialdried over Na2SO4
10. filtrationThe inorganic material was filtered off
11. customthe solvent was removed in vacuo
12. customto give the crude product
13. customPurification via column chromatography

ORD record

ord-101407997f4b408c98a9fbd9e88862ef

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08299267B2