Undecanoyl chloride → 2,4-Diamino-6-ethyl-5-(4-chloro-3-decylcarbonylaminophenyl)pyrimidine

HRID 440972노트

반응식

HRID 440972 반응식
[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[C:11]([NH2:16])[CH:10]=2)=[C:4]([CH2:17][CH3:18])[N:3]=1.[C:19](Cl)(=[O:30])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]>N1C=CC=CC=1.O1CCCC1.O>[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[C:11]([NH:16][C:19]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])=[O:30])[CH:10]=2)=[C:4]([CH2:17][CH3:18])[N:3]=1

참가 물질

6

반응물 2

HCID 87287Undecanoyl chlorideHCID 3307115-(3-Amino-4-chlorophenyl)-6-ethylpyrimidine-2,4-diamine

생성물 1

HCID 199555642,4-Diamino-6-ethyl-5-(4-chloro-3-decylcarbonylaminophenyl)pyrimidine수율 648.1%

시약·촉매·용매 3

HCID 962Water용매2회HCID 1049Pyridine용매HCID 8028Tetrahydrofuran용매2회

실험 절차

Under a nitrogen atmosphere, a solution of 2.5 grams (0.001 mole) of 2,4-diamino-6-ethyl-5-(3-amino-4-chlorophenyl)pyrimidine (prepared in Step B of this Example) in 75 mL of pyridine and 25 mL of tetrahydrofuran was stirred and cooled in an ice bath. To this was added dropwise during a 10 minute period, a solution of 2.2 grams (0.001 mole) of undecanoyl chloride in 50 mL of tetrahydrofuran. The reaction mixture was maintained below about 10° C. throughout the addition. Upon completion of addition, the reaction mixture was stirred under a nitrogen atmosphere for about 4 days. After this time, the reaction mixture was taken up in 100 mL of water and poured into 500 mL of water. The mixture was then extracted with two 200 mL portions of ethyl acetate. The combined extracts were washed with 150 mL of aqueous 10% lithium chloride. The organic layer was dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to a residue. In an effort to remove any excess pyridine, the residue was taken up in 50 mL of toluene, and the solution was concentrated under reduced pressure to a residue. This procedure was repeated two more times. The residue was subjected to column chromatography on silica gel. Elution was accomplished with 10:1 methylene chloride and methanol. The product-containing fractions were combined and concentrated under reduced pressure, yielding 2.8 grams of 2,4-diamino-6-ethyl-5-(4-chloro-3-decylcarbonylaminophenyl)pyrimidine. The NMR spectrum was consistent with the proposed structure.

후처리

  1. temperaturecooled in an ice bath
  2. additionTo this was added dropwise during a 10 minute period
  3. temperatureThe reaction mixture was maintained below about 10° C. throughout the addition
  4. additionUpon completion of addition
  5. extractionThe mixture was then extracted with two 200 mL portions of ethyl acetate
  6. washThe combined extracts were washed with 150 mL of aqueous 10% lithium chloride
  7. dry with materialThe organic layer was dried with magnesium sulfate
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated under reduced pressure to a residue
  10. customIn an effort to remove any excess pyridine
  11. concentrationthe solution was concentrated under reduced pressure to a residue
  12. washElution
  13. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-2ebb8606d1d64eff947c7abc57e7a3eb
출처 데이터셋
uspto-grants-1996_05
특허 번호
US05521192

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