Dimethyl Disulfide → 4-Chloro-5-(methylsulfanyl)-7H-pyrrolo[2,3-D]pyrimidine

Temperature

-78 °C

A solution of 5-bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine (Example 35) (2.53 g, 10 mmol) in anhydrous THF (30 mL) was cooled to -78° C. under argon and a solution of n-butyl lithium (12 mL of 2.3M solution, 25 mmol) was added at such a rate that the reaction temperature remained below -72° C. After the addition, the reaction mixture was stirred at -78° C. for 45 min, a solution of methyl disulfide (0.95 ml, 10 mmol) in tetrahydrofuran (10 mL) was added over a period of 30 minutes maintaining the temperature below -72° C. The reaction mixture was stirred at -78° C. for 2.5 hours then allowed to warm to room temperature. A saturated solution of ammonium chloride (40 mL) was added to the reaction with stirring. The organic layer was separated, the aqueous layer extracted with ethyl acetate (2×40 mL) and the combined organic extracts were dried (MgSO4), filtered and evaporated to obtain a pale yellow solid which was crystallized from EtOH: yield 1.65 g; (70%) m.p. 166°-167° C.

1. customremained below -72° C
2. additionAfter the addition
3. temperaturemaintaining the temperature below -72° C
4. stirringThe reaction mixture was stirred at -78° C. for 2.5 hours
5. temperatureto warm to room temperature
6. stirringwith stirring
7. customThe organic layer was separated
8. extractionthe aqueous layer extracted with ethyl acetate (2×40 mL)
9. dry with materialthe combined organic extracts were dried (MgSO4)
10. filtrationfiltered
11. customevaporated
12. customto obtain a pale yellow solid which
13. customwas crystallized from EtOH

ORD record

ord-e64cd7708b804d81bf0fc4cde9d417b9

Source dataset

uspto-grants-1999_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05864033