Ammonia → N-(6-chloro-7H-purin-2-yl)acetamide

HRID 1647913노트

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HRID 1647913 반응식
C(N1CCCCC1)C.[CH3:9][C:10]([NH:12][C:13]1[NH:19][C:18]2[N:20](C(C)=O)[CH:21]=[N:22][C:17]=2[C:15](=O)[N:14]=1)=[O:11].P(Cl)(Cl)([Cl:28])=O.N>[Cl-].C([N+](CC)(CC)CC)C.C(#N)C.O>[C:10]([NH:12][C:13]1[N:19]=[C:18]2[C:17]([NH:22][CH:21]=[N:20]2)=[C:15]([Cl:28])[N:14]=1)(=[O:11])[CH3:9]

참가 물질

8

반응물 4

HCID 222AmmoniaHCID 13007N-EthylpiperidineHCID 24813Phosphorus oxychlorideHCID 178474472HCID 178474472, 화합물

생성물 1

HCID 6098997N-(6-chloro-7H-purin-2-yl)acetamide수율 89.5%

시약·촉매·용매 3

HCID 5946Tetraethylammonium Chloride촉매HCID 962Water용매HCID 6342Acetonitrile용매

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온도
25 °C

실험 절차

45.0 g (0.27 mol) of tetraethylammonium chloride and 22.8 g (0.2 mol) of N-ethylpiperidine are added to a suspension of 42.6 g (0.18 mol) of 2,9-diacetylguanine in 450 ml of acetonitrile. 165.3 g (1.08 mol) of phosphorus oxychloride are then metered in at a temperature of 0° C. to 5° C. of the reaction mixture. The mixture is stirred at 25° C. for 20 hours, then introduced into 1.25 l of water such that 15° C. is not exceeded and the pH is at the same time kept between 4.8 and 5.5 using 12% strength ammonia solution. The mixture is stirred at 0° C. to 5° C. for 1 hour at a constant pH of 5, then the product is filtered off, washed with water and dried in vacuo at 50° C. 34.1 g of 2-acetamido-6-chloropurine are obtained. The final product is determined with the aid of HPLC on an RP-18 column in a reaction mixture of water, acetonitrile and acetic acid in the ratio 6:1:0.5.

후처리

  1. customare then metered in at a temperature of 0° C. to 5° C. of the reaction mixture
  2. stirringThe mixture is stirred at 0° C. to 5° C. for 1 hour at a constant pH of 5
  3. filtrationthe product is filtered off
  4. washwashed with water
  5. customdried in vacuo at 50° C

출처 및 근거

ORD 기록
ord-b78eead3502141c2a2fb42e1e53b070e
출처 데이터셋
uspto-grants-1995_07
특허 번호
US05434263

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