반응 #82531

반응 방정식

1,1-difluoro-1-(4-chlorophenyl)-3-tributylstannyl-2-propene

tri-2-furylphosphine

2,4-diamino-5-iodo-6-methylpyrimidine

→

2,4-diamino-6-methyl-5-[3,3-difluoro-3-(4-chlorophenyl)-1-propenyl]pyrimidine

용매

N,N-dimethylformamide

반응 조건

후처리

1. 1
   기타is purged with dry nitrogen gas
2. 2
   기타The reaction vessel is then immersed in an oil bath
3. 3
   기타is preheated to 60° C.
4. 4
   온도is maintained for about five minutes
5. 5
   기타The reaction mixture is again purged with dry nitrogen gas
6. 6
   기타is brought to 80°-85° C.
7. 7
   온도is maintained for about 18 hours
8. 8
   workup.ADDITIONAfter this time the reaction mixture is diluted with 200 mL of water
9. 9
   추출extracted with two 200 mL portions of ethyl acetate
10. 10
    세척The combined extracts are then washed with three 100 mL portions of an aqueous solution of 5% lithium chloride
11. 11
    농축The organic layer is concentrated under reduced pressure to a residue
12. 12
    기타The residue is purified by column chromatography

실험 절차

A mixture of 0.04 gram (catalyst) of tri-2-furylphosphine and 0.04 gram (catalyst) of tris(dibenzylidineacetone)dipalladium(0) in 30 mL of N,N-dimethylformamide is purged with dry nitrogen gas and stirred at ambient temperature for five minutes. After this time 1.2 grams (0.0048 mole) of 2,4-diamino-5-iodo-6-methylpyrimidine (prepared in Step B of Example 3) is added in one portion. The reaction vessel is then immersed in an oil bath that is preheated to 60° C. where it is maintained for about five minutes. After this time, 3.1 grams (0.0064 mole) of 1,1-difluoro-1-(4-chlorophenyl)-3-tributylstannyl-2-propene is added in one portion to the reaction mixture. The reaction mixture is again purged with dry nitrogen gas, and the oil bath temperature is brought to 80°-85° C. where it is maintained for about 18 hours. After this time the reaction mixture is diluted with 200 mL of water and extracted with two 200 mL portions of ethyl acetate. The combined extracts are then washed with three 100 mL portions of an aqueous solution of 5% lithium chloride. The organic layer is concentrated under reduced pressure to a residue. The residue is purified by column chromatography, yielding 2,4-diamino-6-methyl-5-[3,3-difluoro-3-(4-chlorophenyl)-1-propenyl]pyrimidine.

출처