Chlorotrimethylsilane → HCID 15789032, compound

Temperature

80 °C

In a 500 ml 4 neck round bottom flask stirring under N2 was charged 1.2 g of Mg (0.050 moles, 1.0 eq) and 5.43 g of chlorotrimethylsilane (0.050 moles, 1.0 eq.) in 50 ml of HMPA (hexamethylphosphoramide) which was heated at 80° C. for 4 hours. To the reaction was added dropwise, 6.4 g of 5-bromopyrimidine (0.040 moles, 0.8 eq.) in 50 ml of HMPA while maintaining the temperature at 80° C. The reaction mixture was stirred for 18 hours at 75° C. after which GLC indicated complete consumption of the 5-bromopyrimidine. The reaction was quenched by adding 100 ml of water, acidified with 10% HCl and extracted with 2×250 ml of ethyl acetate (EtOAc). The acidic aqueous solution was neutralized with 6M NaOH to pH 10 and extracted with 250 ml of EtOAc. The extractions were combined and washed with 4×250 ml aliquots of distilled water. Drying and concentrating afforded 1.2 g of crude product which was purified by flash chromatography with 1:4 ethyl acetate/hexane and afforded 0.6 g of a clear oil (9.8% yield).

1. additionTo the reaction was added dropwise
2. customconsumption of the 5-bromopyrimidine
3. customThe reaction was quenched
4. additionby adding 100 ml of water
5. extractionextracted with 2×250 ml of ethyl acetate (EtOAc)
6. extractionextracted with 250 ml of EtOAc
7. extractionThe extractions
8. washwashed with 4×250 ml aliquots of distilled water
9. customDrying
10. concentrationconcentrating
11. customafforded 1.2 g of crude product which
12. customwas purified by flash chromatography with 1:4 ethyl acetate/hexane

ORD record

ord-ce56526889484d929d156607705dd7d9

Source dataset

uspto-grants-1995_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05451563