Thionyl Chloride → 4-Chloro-7H-pyrrolo(2,3-d)pyrimidine-5-carbonitrile

To a suspension of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbaldehyde oxime (G-3) (865 mg, 4.40 mmol, 1.0 eq) in DCM (20 mL), thionyl chloride (3.1 mL, 43.7 mmol, 10.0 eq) is added and the resulting mixture is stirred at RT overnight. The reaction mixture is concentrated in vacuo. The residue is suspended in water (60 mL) and saturated aqueous NaHCO3 is added to adjust the pH to 4. The solid is collected by filtration, rinsed with water and followed by ethyl acetate to afford the first batch of product. The filtrate is extracted with ethyl acetate (3×50 mL). The combined organic layers are washed with brine, dried over Na2SO4 and filtered. The filtrate is concentrated in vacuo and the residue is combined with the above-obtained solid. The product is re-crystallized in ethyl acetate/hexanes (v/v=1/1) and dried in vacuo to afford the product, 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile (G-4).

1. additionis added
2. concentrationThe reaction mixture is concentrated in vacuo
3. additionsaturated aqueous NaHCO3 is added
4. filtrationThe solid is collected by filtration
5. washrinsed with water
6. customto afford the first batch of product
7. extractionThe filtrate is extracted with ethyl acetate (3×50 mL)
8. washThe combined organic layers are washed with brine
9. dry with materialdried over Na2SO4
10. filtrationfiltered
11. concentrationThe filtrate is concentrated in vacuo
12. customThe product is re-crystallized in ethyl acetate/hexanes (v/v=1/1)
13. customdried in vacuo

ORD 기록

ord-3bf176cabbf944dead63803e35249963

출처 데이터셋

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US09388183B2