Sodium Iodide → 2,4-Dichloro-5-(iodomethyl)pyrimidine

A 500-mL, round-bottom flask equipped with a magnetic stirrer, condenser, and nitrogen-inlet bubbler was charged with sodium iodide (38.5 g, 256.9 mmol) (Aldrich) and acetone (300 mL). After a clear solution was obtained, 2,4-dichloro-5-(chloromethyl)pyrimidine (50.0 g, 253.2 mmol) (from Example 1b supra) was added in one portion. After stirring at room temperature for 20 minutes, the mixture was heated to reflux for 15 minutes. NMR analysis indicated 98% conversion. After cooling to room temperature, the resulting precipitate (sodium chloride) was removed by filtration through a medium-sintered glass funnel and washed with acetone. The combined filtrate and washes were concentrated to a weight of ca. 75 g. The resulting concentrated solution of 2,4-dichloro-5-(iodomethyl)pyrimidine in acetone was diluted with toluene (20 mL). After concentration to a weight of ca.85 g in order to remove the residual acetone, this concentrated solution of 2,4-dichloro-5-(iodomethyl)pyrimidine in toluene was used directly in the next step.

1. customA 500-mL, round-bottom flask equipped with a magnetic stirrer, condenser, and nitrogen-inlet bubbler
2. customAfter a clear solution was obtained
3. temperaturethe mixture was heated
4. temperatureto reflux for 15 minutes
5. temperatureAfter cooling to room temperature
6. customthe resulting precipitate (sodium chloride) was removed by filtration through a medium-sintered glass funnel
7. washwashed with acetone
8. concentrationThe combined filtrate and washes were concentrated to a weight of ca. 75 g
9. additionThe resulting concentrated solution of 2,4-dichloro-5-(iodomethyl)pyrimidine in acetone was diluted with toluene (20 mL)
10. concentrationAfter concentration to a weight of ca
11. custom85 g in order to remove the residual acetone

ORDレコード

ord-c65460f7404d4c359602cdb11f0d47b8

出典データセット

uspto-grants-2006_08

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07098332B2