반응 #82558

반응 방정식

Sodium

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

trans-3-methyl-3-(4-trifluoromethylphenyl)-1-butenylboronic acid

→

trans-2,4-diamino-6-methyl-5-[3-(4-trifluoromethylphenyl)-3-methyl-1-butenyl]pyrimidine

수율 56.5%

용매

ethanol

반응 조건

후처리

1. 1
   기타The reaction mixture was purged with nitrogen
2. 2
   농축After this time the reaction mixture was concentrated under reduced pressure to about 20% of the original volume
3. 3
   workup.ADDITIONpoured into 300 mL of water
4. 4
   온도The mixture was cooled in an ice-bath
5. 5
   여과a solid was collected by filtration
6. 6
   기타The solid was triturated with a mixture of 1:1 petroleum ether
7. 7
   농축concentrated under reduced pressure to a solid residue
8. 8
   기타The solid was recrystallized from 1-propanol and water

실험 절차

Sodium metal, 4.1 grams (0.18 mole), was stirred with 250 mL of ethanol for 30 minutes. After this time 20.0 grams (0.08 mole) of 2,4-diamino-5-iodo-6-methylpyrimidine (prepared in Step B of Example 3), 27.6 grams (0.11 mole) of trans-3-methyl-3-(4-trifluoromethylphenyl)-1-butenylboronic acid, and 9.2 grams (0.008 mole) of tetrakistriphenylphosphine palladium(0) were added. The reaction mixture was purged with nitrogen, and then heated to 80° C. where it stirred for about 28 hours. After this time the reaction mixture was concentrated under reduced pressure to about 20% of the original volume and then poured into 300 mL of water. The mixture was cooled in an ice-bath, and a solid was collected by filtration. The solid was triturated with a mixture of 1:1 petroleum ether:diethyl ether, and then subjected to column chromatography on silica gel using 5% methanol in methylene chloride as the eluant. The product-containing fractions were combined and concentrated under reduced pressure to a solid residue. The solid was recrystallized from 1-propanol and water, yielding 15.2 grams of trans-2,4-diamino-6-methyl-5-[3-(4-trifluoromethylphenyl)-3-methyl-1-butenyl]pyrimidine, mp 182°-185° C. The NMR spectrum was consistent with the proposed structure.

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