Acetyl chloride → HCID 58613284, compound

To a solution of 4-chloro-6-((3S,5R)-3,5-dimethylpiperazin-1-yl)pyrimidine(1, 10.29 g, 45.4 mmol) and DIEA (8.80 g, 68.1 mmol. 1.50 equiv.) in 100 ml DCM was added acetyl chloride (4.03 ml, 56.7 mmol, 1.25 equiv.) at room temperature portionwise over 10 min. The reaction was stirred at room temperature for another 30 min. Aqueous NaHCO3 was added to the reaction and the organic layer was washed with NahCO3 (100 ml×2) followed by saturated aqueous NaCl solution. The organic layer was dried over Organic layer was dried over NacSO4. Removal of solvent left a yellow oil. This oily material was triturated in diethyl ether to afford a white solid. The solid was collected by filtration and the washed with diethyl ether again. The solid was dried under vacuum and was weighted at 11.95 g. The yield is 98.2%. LC/MS (M+1=269.1).

1. washthe organic layer was washed with NahCO3 (100 ml×2)
2. customThe organic layer was dried over Organic layer
3. customwas dried over NacSO4
4. customRemoval of solvent
5. waitleft a yellow oil
6. customThis oily material was triturated in diethyl ether
7. customto afford a white solid
8. filtrationThe solid was collected by filtration
9. washthe washed with diethyl ether again
10. customThe solid was dried under vacuum

ORD record

ord-04d3b191ddfa474fbc0637945f1dc55a

Source dataset

uspto-grants-2008_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07329652B2